New Chicagoan Here!
Member since 2026 · 10 posts · 7 votes
New Chicagoan Here!
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Aaron ZimmermanBusiness Member
Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votesWelcome! I'd encourage you to go to some local meetups like cash flow breakfast club, Chicago multifamily club, and many more to build your network.
I would also be listening to the straight up Chicago investor podcast as it has Local info and guests.
Brick House CPAs53 Reviews
26 Replies
- Lender · TX · Member since 2026 · 164 posts · 67 votes3mo
We help real estate investors secure fast capital for fix-and-flips, rental acquisitions, and short-term bridge deals.
- Investor · Hinton, WV · Member since 2026 · 80 posts · 22 votes3mo
Quote from @Seemaab Mujtaba:
Hello everyone. I'm a resident of Chicago and starting my journey in the investing space.
I have experience managing and maintaining an 8-unit multi-family building that belonged to my father, but I've never purchased anything myself. I've saved some cash and feel it's time to start making some moves.
I'm hoping to find great mentors and learn as much as possible before I start. What appeals to me is rental properties and fix and flips.
I would really appreciate any and all resources that would benefit a newbie like myself.
Welcome and let me stop you right there on the word 'newbie.'
Managing an 8-unit building is not beginner experience. You understand tenant relations, maintenance, occupancy, and operations things most first-time investors have to learn the hard way after they've already bought something. You're starting with an edge, own that.
Now, between rentals and fix-and-flips they're both solid, but they require different mindsets and capital strategies. Rentals are about patience and cash flow. Flips are about speed, execution, and knowing your numbers cold. Chicago is actually a strong market for both if you know which neighborhoods to focus on.
A few things I'd point you toward as you build your foundation:
- BiggerPockets is the most practical community and resource hub for exactly where you are right now
- Start analyzing real deals on the MLS even before you're ready to buy the reps you get running numbers will sharpen your judgment faster than any course
- Connect with a local investor-friendly agent and a hard money lender early, even if you don't need them yet
The cash you've saved is your starting position. The knowledge you build in the next 90 days determines how well you deploy it.
What's your timeline looking like, and do you have a specific side of Chicago you're most fam- Member since 2026 · 10 posts · 7 votes3mo
Quote from @Luran James:
Quote from @Seemaab Mujtaba:
Hello everyone. I'm a resident of Chicago and starting my journey in the investing space.
I have experience managing and maintaining an 8-unit multi-family building that belonged to my father, but I've never purchased anything myself. I've saved some cash and feel it's time to start making some moves.
I'm hoping to find great mentors and learn as much as possible before I start. What appeals to me is rental properties and fix and flips.
I would really appreciate any and all resources that would benefit a newbie like myself.
Welcome and let me stop you right there on the word 'newbie.'
Managing an 8-unit building is not beginner experience. You understand tenant relations, maintenance, occupancy, and operations things most first-time investors have to learn the hard way after they've already bought something. You're starting with an edge, own that.
Now, between rentals and fix-and-flips they're both solid, but they require different mindsets and capital strategies. Rentals are about patience and cash flow. Flips are about speed, execution, and knowing your numbers cold. Chicago is actually a strong market for both if you know which neighborhoods to focus on.
A few things I'd point you toward as you build your foundation:
- BiggerPockets is the most practical community and resource hub for exactly where you are right now
- Start analyzing real deals on the MLS even before you're ready to buy the reps you get running numbers will sharpen your judgment faster than any course
- Connect with a local investor-friendly agent and a hard money lender early, even if you don't need them yet
The cash you've saved is your starting position. The knowledge you build in the next 90 days determines how well you deploy it.
What's your timeline looking like, and do you have a specific side of Chicago you're most fam
Hi Luran. Thank you for the kind words and insights.
I'm most familiar with the north side of Chicago, as I grew up there.Should I be focusing my attention towards certain areas? So that I can become more familiar with the property market trends there? That does make sense, rather than overwhelming myself with different markets.
I've never heard the term 'investor-friendly agent' but I now understand that's what I was hoping to find at some point. How should I go about finding one? Also, how would I access the MLS? - Investor · Hinton, WV · Member since 2026 · 80 posts · 22 votes3mo
Quote from @Seemaab Mujtaba:
Quote from @Luran James:
Quote from @Seemaab Mujtaba:
Hello everyone. I'm a resident of Chicago and starting my journey in the investing space.
I have experience managing and maintaining an 8-unit multi-family building that belonged to my father, but I've never purchased anything myself. I've saved some cash and feel it's time to start making some moves.
I'm hoping to find great mentors and learn as much as possible before I start. What appeals to me is rental properties and fix and flips.
I would really appreciate any and all resources that would benefit a newbie like myself.
Welcome and let me stop you right there on the word 'newbie.'
Managing an 8-unit building is not beginner experience. You understand tenant relations, maintenance, occupancy, and operations things most first-time investors have to learn the hard way after they've already bought something. You're starting with an edge, own that.
Now, between rentals and fix-and-flips they're both solid, but they require different mindsets and capital strategies. Rentals are about patience and cash flow. Flips are about speed, execution, and knowing your numbers cold. Chicago is actually a strong market for both if you know which neighborhoods to focus on.
A few things I'd point you toward as you build your foundation:
- BiggerPockets is the most practical community and resource hub for exactly where you are right now
- Start analyzing real deals on the MLS even before you're ready to buy the reps you get running numbers will sharpen your judgment faster than any course
- Connect with a local investor-friendly agent and a hard money lender early, even if you don't need them yet
The cash you've saved is your starting position. The knowledge you build in the next 90 days determines how well you deploy it.
What's your timeline looking like, and do you have a specific side of Chicago you're most fam
Hi Luran. Thank you for the kind words and insights.
I'm most familiar with the north side of Chicago, as I grew up there.Should I be focusing my attention towards certain areas? So that I can become more familiar with the property market trends there? That does make sense, rather than overwhelming myself with different markets.
I've never heard the term 'investor-friendly agent' but I now understand that's what I was hoping to find at some point. How should I go about finding one? Also, how would I access the MLS?I will message you get you more further
- 3moAaron ZimmermanBusiness MemberAccountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
Welcome! I'd encourage you to go to some local meetups like cash flow breakfast club, Chicago multifamily club, and many more to build your network.
I would also be listening to the straight up Chicago investor podcast as it has Local info and guests.
Brick House CPAs53 Reviews- Member since 2026 · 10 posts · 7 votes3mo
Quote from @Aaron Zimmerman:
Welcome! I'd encourage you to go to some local meetups like cash flow breakfast club, Chicago multifamily club, and many more to build your network.
I would also be listening to the straight up Chicago investor podcast as it has Local info and guests.
Thank you Andrew! I'll definitely tune in to these!
- 3moEudith VacioPro MemberReal Estate Agent · Chicago & NWI · Member since 2015 · 860 posts · 521 votes
Yes, lets goo! love the idea of making your first move and the best way to get started is house-hacking but if you want to buy a rental property thats definitely do-able if you have enough for a hefty down payment + and if you want to do a flip, most lenders will lend with a 20% down payment and that will go down with more experience.
Where in Chicago were you looking to do this?
- Member since 2026 · 10 posts · 7 votes3mo
Quote from @Eudith Vacio:
Yes, lets goo! love the idea of making your first move and the best way to get started is house-hacking but if you want to buy a rental property thats definitely do-able if you have enough for a hefty down payment + and if you want to do a flip, most lenders will lend with a 20% down payment and that will go down with more experience.
Where in Chicago were you looking to do this?
Thank you for your message Eudith! To be honest, I'm a bit confused on which areas I SHOULD be looking into. I've considered the south and west sides of Chicago, as well as the western suburbs. However, I don't have enough knowledge to back up why, besides the lower prices of properties in these areas. I would like to understand what areas are up and coming, where the rent prices are in an uptrend.
I might be looking through the wrong lens though, and that's something I want to work on or get advice on before I even start looking at individual properties.
- Solo 401k Expert · Anaheim Hills, CA · Member since 2012 · 18k+ posts · 6k+ votes3mo
Hello Seemaab, It's great to have you here!
Set up keyword alerts to be notified of the topics that interest you: http://www.biggerpockets.com/alerts
Lots of luck.
- Member since 2026 · 10 posts · 7 votes3mo
Quote from @Dmitriy Fomichenko:
Hello Seemaab, It's great to have you here!
Set up keyword alerts to be notified of the topics that interest you: http://www.biggerpockets.com/alerts
Lots of luck.
Hi Dmitriy! Thank you for letting me know about this! I'll definitely give it a try.
- Member since 2026 · 70 posts · 24 votes3mo
Welcome Seemaab! Managing an 8 unit building gives you more practical experience than most new investors have when they start. You already know what tenant issues, maintenance calls, and turnover actually feel like. That is a real advantage.
A few things worth knowing before you buy your first property:
Understand your numbers before you close. Know what the property should generate in rent, what the realistic expenses are, and what your margin looks like after taxes, insurance, and maintenance. A deal that looks good on paper can look very different after the first year of ownership.
Start with what you can manage. Your multifamily background is valuable but self managing a rental you own is different from managing one that belongs to someone else. Know your bandwidth before you scale.
Get your systems in place from day one. Leases, records, tenant communications, expense tracking. The landlords who struggle are usually the ones who waited too long to get organized.
BiggerPockets itself is one of the best free resources available. A local REIA in Chicago is also worth attending; in person connections accelerate everything.
Good luck. You are starting from a stronger position than you probably realize.
- Member since 2026 · 10 posts · 7 votes3mo
Quote from @Kim Gray:
Welcome Seemaab! Managing an 8 unit building gives you more practical experience than most new investors have when they start. You already know what tenant issues, maintenance calls, and turnover actually feel like. That is a real advantage.
A few things worth knowing before you buy your first property:
Understand your numbers before you close. Know what the property should generate in rent, what the realistic expenses are, and what your margin looks like after taxes, insurance, and maintenance. A deal that looks good on paper can look very different after the first year of ownership.
Start with what you can manage. Your multifamily background is valuable but self managing a rental you own is different from managing one that belongs to someone else. Know your bandwidth before you scale.
Get your systems in place from day one. Leases, records, tenant communications, expense tracking. The landlords who struggle are usually the ones who waited too long to get organized.
BiggerPockets itself is one of the best free resources available. A local REIA in Chicago is also worth attending; in person connections accelerate everything.
Good luck. You are starting from a stronger position than you probably realize.
Hello Kim! I totally agree with you. Having systems in place for all these things lets you spend time on things that actually deserve it. I actually currently work for a tenant application and screening platform as a software engineer, so I think this might be one of the things I do have a fair background in, as well.
Hmm...now that I think about it, I just might be cut out for this industry more than I thought. I suppose evaluating market trends and properties is my biggest gap.
- 3moVictor SoBusiness MemberReal Estate Agent · Chicago, IL · Member since 2017 · 324 posts · 192 votes
Quote from @Seemaab Mujtaba:
Hello everyone. I'm a resident of Chicago and starting my journey in the investing space.
I have experience managing and maintaining an 8-unit multi-family building that belonged to my father, but I've never purchased anything myself. I've saved some cash and feel it's time to start making some moves.
I'm hoping to find great mentors and learn as much as possible before I start. What appeals to me is rental properties and fix and flips.
I would really appreciate any and all resources that would benefit a newbie like myself.
Hey! Quick question - I know you said you haven’t bought anything for yourself and you have some money saved up. What’s your current living situation? Have you considered house hacking? To me, for your very first deal, househacking is the best intro to investing and essentially landlording on training wheels. I’ve househacked my first few properties, and more and more I realize that getting into a 2-4 unit with only 5% down is just crazy. I’m in my 40s now with a family and 2 kids. I’m still trying to find ways to househack and convince my wife to do so.
Victor So Real Estate LLC517 Reviews- Member since 2026 · 10 posts · 7 votes3mo
Quote from @Victor So:
Quote from @Seemaab Mujtaba:
Hello everyone. I'm a resident of Chicago and starting my journey in the investing space.
I have experience managing and maintaining an 8-unit multi-family building that belonged to my father, but I've never purchased anything myself. I've saved some cash and feel it's time to start making some moves.
I'm hoping to find great mentors and learn as much as possible before I start. What appeals to me is rental properties and fix and flips.
I would really appreciate any and all resources that would benefit a newbie like myself.
Hey! Quick question - I know you said you haven’t bought anything for yourself and you have some money saved up. What’s your current living situation? Have you considered house hacking? To me, for your very first deal, househacking is the best intro to investing and essentially landlording on training wheels. I’ve househacked my first few properties, and more and more I realize that getting into a 2-4 unit with only 5% down is just crazy. I’m in my 40s now with a family and 2 kids. I’m still trying to find ways to househack and convince my wife to do so.
Hello Victor! I'm currently renting an apartment, but I've absolutely considered living in a multi-family if it was worth it. I understand that there might be some tax breaks if I live in one of the units I own, but I'll have to re-check that. And yes, I'm in the same boat as my wife will have to be convinced lol
- Real Estate Broker · Chicago, IL · Member since 2014 · 2k+ posts · 1k+ votes3mo
Quote from @Seemaab Mujtaba:
Hello everyone. I'm a resident of Chicago and starting my journey in the investing space.
I have experience managing and maintaining an 8-unit multi-family building that belonged to my father, but I've never purchased anything myself. I've saved some cash and feel it's time to start making some moves.
I'm hoping to find great mentors and learn as much as possible before I start. What appeals to me is rental properties and fix and flips.
I would really appreciate any and all resources that would benefit a newbie like myself.
Welcome to the forum. Under Real Estate Classified forum you'll find local meetings and events.
- Memphis, TN · Member since 2024 · 180 posts · 223 votes3mo
You're already ahead of a lot of first-time investors.
Managing and maintaining an 8-unit property gives you exposure to the part of real estate that many people don't fully understand until after they buy their first deal.That's really great stuff.
If I could give one piece of advice, it would be to focus on learning how to analyze deals and choose one strategy to start with. Rentals and flips can both be great, but it's usually easier to gain traction when you're not trying to do everything at once.
I'd also spend as much time networking as possible. Building relationships with active investors, lenders, contractors, and agents can set you up for success and get you across that learning curve quicker.
Best of luck!
- Real Estate Broker · New York, NY · Member since 2020 · 2k+ posts · 1k+ votes3mo
Hey Seemab,
I second Aaron’s advice on attending meetups. It’s honestly one of the most underrated ways to get traction early on. You end up meeting other investors, agents, lenders, and contractors in a pretty natural way, and those relationships tend to be way more valuable than just reading or researching on your own.
Being in the room with people who are actively doing deals in your market also helps you get a much clearer sense of what’s realistic right now versus what looks good on paper.
I’m based in NYC and always happy to connect and share ideas. My DMs are open if you ever want to chat or bounce some ideas around.- Member since 2026 · 10 posts · 7 votes3mo
Quote from @Mohammed Rahman:
Hey Seemab,
I second Aaron’s advice on attending meetups. It’s honestly one of the most underrated ways to get traction early on. You end up meeting other investors, agents, lenders, and contractors in a pretty natural way, and those relationships tend to be way more valuable than just reading or researching on your own.
Being in the room with people who are actively doing deals in your market also helps you get a much clearer sense of what’s realistic right now versus what looks good on paper.
I’m based in NYC and always happy to connect and share ideas. My DMs are open if you ever want to chat or bounce some ideas around.
Thank you for the tip Mohammed! Go Knicks! I've signed up at chicagoreia.org and see a few events coming up. I'll do my best to attend!
- Real Estate Agent · Chicago, IL · Member since 2017 · 2k+ posts · 2k+ votes3mo
Welcome, feel free to PM if want to chat on a call happy to network! I have a 4 unit I house hack in rogers park it works great. House hacking is easiest way to get into owning yourself as can buy low down only 5% and I would say 99% of my first time buyer clients get in this way. Managing an 8 unit will make these buildings feel easy. I did a flip last year which worked out for a six figure net but the profit was forsure partially driven by appreciation during the hold period, the flip market is actually really tight right now not a ton of spread with so much competition out there currently, just buying low down house hack that you later once move turn into a rental in good growing areas is the easiest path.
- Member since 2026 · 10 posts · 7 votes3mo
Quote from @Henry Lazerow:
Welcome, feel free to PM if want to chat on a call happy to network! I have a 4 unit I house hack in rogers park it works great. House hacking is easiest way to get into owning yourself as can buy low down only 5% and I would say 99% of my first time buyer clients get in this way. Managing an 8 unit will make these buildings feel easy. I did a flip last year which worked out for a six figure net but the profit was forsure partially driven by appreciation during the hold period, the flip market is actually really tight right now not a ton of spread with so much competition out there currently, just buying low down house hack that you later once move turn into a rental in good growing areas is the easiest path.
Thanks Henry! Looking at prices myself, I felt similar about flipping currently. I'd be happy to connect soon and discuss more!
- Investor · Hinton, WV · Member since 2026 · 80 posts · 22 votes3mo
Quote from @Seemaab Mujtaba:
Hello everyone. I'm a resident of Chicago and starting my journey in the investing space.
I have experience managing and maintaining an 8-unit multi-family building that belonged to my father, but I've never purchased anything myself. I've saved some cash and feel it's time to start making some moves.
I'm hoping to find great mentors and learn as much as possible before I start. What appeals to me is rental properties and fix and flips.
I would really appreciate any and all resources that would benefit a newbie like myself.
Welcome to the investing space, and congratulations on taking the first step. You're actually starting from a stronger position than many people because managing an 8-unit property has already given you exposure to the realities of ownership and operations.
Since rental properties and fix-and-flips appeal to you, I'd recommend spending time analyzing deals, understanding your local market, and building relationships with experienced investors before making your first purchase. A good deal bought right can make all the difference.
Some resources that helped many investors get started include BiggerPockets podcasts, books like "The Book on Rental Property Investing" and "The Book on Flipping Houses," as well as attending local REIA meetings and networking events around Chicago.
Most importantly, don't feel pressured to rush into your first deal. Focus on learning, running the numbers conservatively, and surrounding yourself with people who are already doing what you want to do.
You're already ahead of many beginners because you've had firsthand experience with multifamily operations through your father's property. Keep learning, stay patient, and I'm confident you'll do well.
Wishing you much success on your journey. Feel free to reach out if you'd ever like to discuss rentals, fix-and-flips, or exchange ideas with fellow investors. Always happy to connect and share insights.
- 3moWale LawalBusiness MemberReal Estate Broker · Houston | Dallas | Austin, TX · Member since 2018 · 5k+ posts · 2k+ votes
You are lucky in that way because learning from running an 8 unit building offers many things that you cannot learn from books. My suggestion is that you continue to look for good deals, make connections in the area, and start with a reliable rental rather than flipping properties.
Good luck!
NETWORTH BUILDERS5236 Reviews - 3moAmit PatelBusiness MemberProperty Manager · Bartlett, IL · Member since 2025 · 141 posts · 57 votes
Hey Seemaab,Welcome to the group and to Chicago investing. Having already managed and maintained an 8-unit building gives you a real head start. That hands on experience with tenants, maintenance, and operations is going to serve you well.
For rentals, I’d focus first on understanding the numbers in your specific neighborhoods cash flow after taxes, insurance, and realistic maintenance. Chicago can be a strong market for buy-and-hold if you buy right, but the tax and insurance environment rewards people who run conservative numbers and keep good systems in place.
Fix andflips are flashier but usually riskier as a first move. A lot of people do better starting with a smaller rental or even a house hack, then using the experience and cash flow to take on rehabs later. You already know what it takes to keep a building running, so lean into that strength instead of jumping straight into the higher-risk side.
As far as resources, BiggerPockets is still one of the best places to learn (their rental property investing book is solid for beginners). Locally, check out some of the Chicago-area real estate investor meetups they’re great for finding mentors and getting real talk about what’s actually working in the city right now versus what worked five years ago. You can ask Ai to give you a calendar of all the meet ups it can find in your area for that month or 2 months in advance and select the ones taht works for you.
If you want to connect or talk through what you’re looking, feel free to message me. Happy to talk!
Casanomy Property Management562 Reviews - Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes3mo
What's up @Seemaab Mujtaba! Welcome to the real estate space! You couldn't have picked a better city than Chicago to get started - very biased here.
Network, network, network when you are getting going. There are several events listed here on BP: https://www.biggerpockets.com/forums/521-real-estate-events-...
Also, I have a list of a ton of other chicago events that I'd be happy to share.
Are you looking at any specific areas for the first purchase?
Quality Builders4.966 Reviews- Member since 2026 · 10 posts · 7 votes3mo
Quote from @Jonathan Klemm:
What's up @Seemaab Mujtaba! Welcome to the real estate space! You couldn't have picked a better city than Chicago to get started - very biased here.
Network, network, network when you are getting going. There are several events listed here on BP: https://www.biggerpockets.com/forums/521-real-estate-events-...
Also, I have a list of a ton of other chicago events that I'd be happy to share.
Are you looking at any specific areas for the first purchase?
@Jonathan Klemm Thank you so much! As far as specific areas, I've just learned about the concept of a 'buy box', so I was actually starting to piece that together.
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