Hey yo! Long time listener first time caller.I’m 48 years old and tired of making other people money. My grandparents had about 20 rentals back in the day. Unfortunately, they were lost during the recession. I’m ready to move on and start my own adventure in renting. I’m struggling with how to analyze a property correctly. That has given me some analysis paralysis on taking the next step.
I guess what I’m asking is how do I know if a deal is good? How do I find a trustworthy mentor that doesn’t cost an arm and a leg?
Thank you for taking time to read. I look forward to hearing your guys advice.
Darrell
Real Estate Investor
A “good deal” usually comes down to simple fundamentals: buying below realistic value, understanding repairs, knowing local rents/demand, and leaving enough margin for mistakes. Keep it conservative and don’t force deals. As for mentors, be careful of anyone selling shortcuts or hype. Find someone actively doing deals who’s willing to answer questions, let you observe, or even partner on smaller opportunities. Real mentorship usually starts through relationships and conversations, not giant coaching payments.
Hey yo! Long time listener first time caller.I’m 48 years old and tired of making other people money. My grandparents had about 20 rentals back in the day. Unfortunately, they were lost during the recession. I’m ready to move on and start my own adventure in renting. I’m struggling with how to analyze a property correctly. That has given me some analysis paralysis on taking the next step.
I guess what I’m asking is how do I know if a deal is good? How do I find a trustworthy mentor that doesn’t cost an arm and a leg?
Thank you for taking time to read. I look forward to hearing your guys advice.
Darrell
Real Estate Investor
Hey @Darrell Gibson, welcome to the BP Forum! Which property types interest you most, SFR, 2-4 MF, or 5+ MF? What is your price range/down payment amount? Are you looking for turn-key properties or something along the lines of a "fixer upper"? Are you looking for properties in your local market or somewhere else?
Hello Mr. Green,
I am primarily interested in single family and small duplexes. I have been preapproved for $250K. I would like to keep the mortgage payment to something below $1200-$1500. Turn-key would be ideal, but I have some skill for a minor fixer upper. I would like to stay local.
Hello Mr. Green,
I am primarily interested in single family and small duplexes. I have been preapproved for $250K. I would like to keep the mortgage payment to something below $1200-$1500. Turn-key would be ideal, but I have some skill for a minor fixer upper. I would like to stay local.
@Darrell Gibson Are you planning to house hack or would that property on Lincolnway be a true SF rental?
Hello Mr. Green,
I am primarily interested in single family and small duplexes. I have been preapproved for $250K. I would like to keep the mortgage payment to something below $1200-$1500. Turn-key would be ideal, but I have some skill for a minor fixer upper. I would like to stay local.
@Darrell Gibson Are you planning to house hack or would that property on Lincolnway be a true SF rental?
It would be a true SF rental. My wife is not down for the house hacking. She is a party pooper.
Hello Mr. Green,
I am primarily interested in single family and small duplexes. I have been preapproved for $250K. I would like to keep the mortgage payment to something below $1200-$1500. Turn-key would be ideal, but I have some skill for a minor fixer upper. I would like to stay local.
@Darrell Gibson Are you planning to house hack or would that property on Lincolnway be a true SF rental?
It would be a true SF rental. My wife is not down for the house hacking. She is a party pooper.
@Darrell Gibson Good luck at the event. As for the SF rental in Mishawaka, how realistic is renting it at $2,200? I did a quick search and I'd guess you'd max out around $2k. Even at $2k, I think this could be a good deal, as long as you don't have to do too much rehab.
Hello Mr. Green,
I am primarily interested in single family and small duplexes. I have been preapproved for $250K. I would like to keep the mortgage payment to something below $1200-$1500. Turn-key would be ideal, but I have some skill for a minor fixer upper. I would like to stay local.
@Darrell Gibson Are you planning to house hack or would that property on Lincolnway be a true SF rental?
It would be a true SF rental. My wife is not down for the house hacking. She is a party pooper.
@Darrell Gibson Good luck at the event. As for the SF rental in Mishawaka, how realistic is renting it at $2,200? I did a quick search and I'd guess you'd max out around $2k. Even at $2k, I think this could be a good deal, as long as you don't have to do too much rehab.
I think $2000 is doable but would be the top of the range. Unless it was in a prime location and was renovated. I used to pay that in rent.
Hello Mr. Green,
I am primarily interested in single family and small duplexes. I have been preapproved for $250K. I would like to keep the mortgage payment to something below $1200-$1500. Turn-key would be ideal, but I have some skill for a minor fixer upper. I would like to stay local.
@Darrell Gibson Are you planning to house hack or would that property on Lincolnway be a true SF rental?
It would be a true SF rental. My wife is not down for the house hacking. She is a party pooper.
@Darrell Gibson Good luck at the event. As for the SF rental in Mishawaka, how realistic is renting it at $2,200? I did a quick search and I'd guess you'd max out around $2k. Even at $2k, I think this could be a good deal, as long as you don't have to do too much rehab.
I think $2000 is doable but would be the top of the range. Unless it was in a prime location and was renovated. I used to pay that in rent.
@Darrell Gibson got it. should still be a doable deal at $2k. Have you checked into how you'd finance the purchase?
Hello Mr. Green,
I am primarily interested in single family and small duplexes. I have been preapproved for $250K. I would like to keep the mortgage payment to something below $1200-$1500. Turn-key would be ideal, but I have some skill for a minor fixer upper. I would like to stay local.
@Darrell Gibson Are you planning to house hack or would that property on Lincolnway be a true SF rental?
It would be a true SF rental. My wife is not down for the house hacking. She is a party pooper.
@Darrell Gibson Good luck at the event. As for the SF rental in Mishawaka, how realistic is renting it at $2,200? I did a quick search and I'd guess you'd max out around $2k. Even at $2k, I think this could be a good deal, as long as you don't have to do too much rehab.
I think $2000 is doable but would be the top of the range. Unless it was in a prime location and was renovated. I used to pay that in rent.
@Darrell Gibson got it. should still be a doable deal at $2k. Have you checked into how you'd finance the purchase?
I was preapproved for a $250K loan with zero down. The issue is that it is a VA loan. It comes with the requirement to live in it for a year. I am not sure I want to chance it for a rental.
Hello Mr. Green,
I am primarily interested in single family and small duplexes. I have been preapproved for $250K. I would like to keep the mortgage payment to something below $1200-$1500. Turn-key would be ideal, but I have some skill for a minor fixer upper. I would like to stay local.
@Darrell Gibson Are you planning to house hack or would that property on Lincolnway be a true SF rental?
It would be a true SF rental. My wife is not down for the house hacking. She is a party pooper.
@Darrell Gibson Good luck at the event. As for the SF rental in Mishawaka, how realistic is renting it at $2,200? I did a quick search and I'd guess you'd max out around $2k. Even at $2k, I think this could be a good deal, as long as you don't have to do too much rehab.
I think $2000 is doable but would be the top of the range. Unless it was in a prime location and was renovated. I used to pay that in rent.
@Darrell Gibson got it. should still be a doable deal at $2k. Have you checked into how you'd finance the purchase?
I was preapproved for a $250K loan with zero down. The issue is that it is a VA loan. It comes with the requirement to live in it for a year. I am not sure I want to chance it for a rental.
@Darrell Gibson you should be able to get a DSCR loan from a local bank/credit union that underwrites using the cash flow from the property and doesn't require you to live in it.
Welcome to BP Darrell! Just to confirm, are you looking for rentals or flips/wholesale?
Welcome to BP Darrell! Just to confirm, are you looking for rentals or flips/wholesale?
I am mainly looking for long term rentals. I am open to small flips or renovations.

Hi Darrell,
Honestly, I think more people deal with analysis paralysis than they admit. Especially early on when everything feels high stakes and everybody online sounds like they’ve got it all figured out.
One thing I’ve been learning lately is this...
A “good deal” isn’t just about whether the numbers work on paper.
The bigger question eventually becomes:
Can this deal survive pressure?
And honestly... can YOU survive the pressure that comes with it?
Because pressure changes everything:
vacancy,
maintenance,
management,
life events,
unexpected expenses,
communication breakdowns,
reserves disappearing faster than expected...
A lot of deals look amazing before pressure arrives.
That’s part of what separates an investor from an operator.
As for mentorship, I think that word gets thrown around a lot these days. You don’t necessarily need to spend thousands of dollars to begin learning this space.
We live in a time where books, podcasts, communities, lender interviews, local REI meetups and even AI tools have made learning more accessible than ever before.
The key is pairing learning with small actionable steps forward.
Talk to local investors.
Walk properties.
Ask questions.
Learn how lenders think.
Study both successful deals and failed ones.
And don’t underestimate the value of simply observing how experienced people operate under pressure.
You’re not behind brother. You’re learning.
And honestly, taking your time to understand the environment before forcing a deal may save you a whole lot of pain long term.
Keep going.
-Sarge

Hi Darrell,
Honestly, I think more people deal with analysis paralysis than they admit. Especially early on when everything feels high stakes and everybody online sounds like they’ve got it all figured out.
One thing I’ve been learning lately is this...
A “good deal” isn’t just about whether the numbers work on paper.
The bigger question eventually becomes:
Can this deal survive pressure?
And honestly... can YOU survive the pressure that comes with it?
Because pressure changes everything:
vacancy,
maintenance,
management,
life events,
unexpected expenses,
communication breakdowns,
reserves disappearing faster than expected...
A lot of deals look amazing before pressure arrives.
That’s part of what separates an investor from an operator.
As for mentorship, I think that word gets thrown around a lot these days. You don’t necessarily need to spend thousands of dollars to begin learning this space.
We live in a time where books, podcasts, communities, lender interviews, local REI meetups and even AI tools have made learning more accessible than ever before.
The key is pairing learning with small actionable steps forward.
Talk to local investors.
Walk properties.
Ask questions.
Learn how lenders think.
Study both successful deals and failed ones.
And don’t underestimate the value of simply observing how experienced people operate under pressure.
You’re not behind brother. You’re learning.
And honestly, taking your time to understand the environment before forcing a deal may save you a whole lot of pain long term.
Keep going.
-Sarge
Thank you for this reply. It is encouraging to hear. I am going to look for some local meetups or landlord groups.
Hey yo! Long time listener first time caller.I’m 48 years old and tired of making other people money. My grandparents had about 20 rentals back in the day. Unfortunately, they were lost during the recession. I’m ready to move on and start my own adventure in renting. I’m struggling with how to analyze a property correctly. That has given me some analysis paralysis on taking the next step.
I guess what I’m asking is how do I know if a deal is good? How do I find a trustworthy mentor that doesn’t cost an arm and a leg?
Thank you for taking time to read. I look forward to hearing your guys advice.
Darrell
Real Estate Investor
You are in a great spot for cash flow. Would definitely recommend something you can try to manage yourself. That's how you learn. Look at the standard lease contracts for your area and try to do some of the work yourself. Just think about all the places you have lived and all the landlords you have dealt with. Then think about how much of a better job you could have done and how. Then do it. Keep expenses low and buy a very standard steady eddy property to start. A single family or duplex in a nice area that you would want to live in the house and area. That's the best way to learn in my opinion.
A “good deal” usually comes down to simple fundamentals: buying below realistic value, understanding repairs, knowing local rents/demand, and leaving enough margin for mistakes. Keep it conservative and don’t force deals. As for mentors, be careful of anyone selling shortcuts or hype. Find someone actively doing deals who’s willing to answer questions, let you observe, or even partner on smaller opportunities. Real mentorship usually starts through relationships and conversations, not giant coaching payments.
Darrell, analysis paralysis is real and I'm fighting the same battle. I am finding the honest answer is you learn to analyze by doing it over and over until the numbers start to feel familiar. Have you run the numbers on any specific deals yet even if you didn't pursue them?
Darrell, analysis paralysis is real and I'm fighting the same battle. I am finding the honest answer is you learn to analyze by doing it over and over until the numbers start to feel familiar. Have you run the numbers on any specific deals yet even if you didn't pursue them?
I have tried to run the numbers. Honestly some of it seems Greek to me. I ran one and it seemed to work by looking at the numbers. I just didn't trust myself to act on them.
@Darrell Gibson What was the deal you ran?
I ran some numbers based on what you posted. Here is what I see. That amount of cash flow looks very good right out of the gate. I'd guess there is some additional rehab costs to account for to start.

I ran some numbers based on what you posted. Here is what I see. That amount of cash flow looks very good right out of the gate. I'd guess there is some additional rehab costs to account for to start.

Thank you! At least I feel like I can trust my numbers for the most part. I am working with my agent to find either a good deal or something that is not overpriced.
Hey @Darrell Gibson
I'm working toward my first multifamily deal too, so this one lands for me. What I've found with me is that the paralysis usually isn't a knowledge gap. It's treating the first deal like the only deal.
The thing that's helped me most is analyzing ten real listings in a month with no intention of buying any of them. Rough numbers, ten minutes each. You're not hunting for the one. You're building the reps that make a good deal obvious when it shows up. Honestly, that confidence comes from the tenth analysis, not from one more course.
On your grandparents losing the rentals in the recession; sorry to hear about that, I'd keep that point close. It's the reason to underwrite the downside first: what rent and what vacancy still lets the property carry itself. A deal that survives the bad case is one you can actually pull the trigger on.
I've found that you don't need to pay for a mentor to start that. You need a second set of eyes at the moment you're about to act. Just my 2 cents. Best of luck, and happy to help as I've been there...we'll get that 1st deal!
Fernando
Darrell what a story and what a reason to start. Carrying that family history into your own journey is not a burden — it is motivation most investors never have.
On analysis paralysis — this is the most common reason good investors never become actual investors. Here is the truth about deal analysis that nobody tells you upfront.
You will never feel completely certain. The goal is not certainty. The goal is informed confidence. Run the numbers until you understand them — not until they feel perfect.
The numbers that matter most on a first rental:
Monthly rent minus mortgage, taxes, insurance, and a reserve for repairs and vacancy. If what is left is positive or breaks even in a market with appreciation potential — look harder at that deal. The 1% rule — monthly rent at least 1% of purchase price — is a quick filter not a final answer.
On finding a mentor without paying for one — your grandparents' story is your opening line in every conversation. Real estate investors respond to legacy. Find your local REIA group in the South Bend area. Show up every month. Be genuinely curious. Ask experienced investors about their first deal. Most people love telling that story and the relationship builds naturally from there.
BiggerPockets itself is a mentor at scale. The search function here has answered every question you are afraid to ask.
Analysis paralysis breaks the moment you make an offer. Not before.
You can absolutely do this Darrell. Your grandparents started something. You finish it
Most investors experience analysis paralysis at the beginning.
A “good deal” usually comes down to:
cash flow, downside risk, location quality, and having enough margin for mistakes.
The biggest mistake is waiting for the “perfect” deal instead of learning by doing smaller deals first.
Hi Darrell, We actually had a property in Mishawaka that we were handling (after it was foreclosed on) back during the last crash...somewhere between 2009 and 2012. I saw the name of the town and I had to respond. To actually answer your question, I think you have to ask yourself what you're wanting to do. Own rentals with tenants and toilets? Flip houses? New spec construction? Private lending? Performing of Nonperforming loans? What is it you really want to do? I think it is hard to find your niche. I came in with a strong background in banking/lending and my wife's degree is in interior design, so we had a solid foundation. I realized that 2am calls about the air being out was not for me and I stuck to what I had my entire career in...private lending, mortgage, and nonperforming loans. Once you know that, you can take stock in what you bring to the table as a skill set. Construction? Capital? Finding deals? If you know what you know and realize what you don't know, it helps finding partners to learn from that have those skill sets you don't. The next thing is to do a deep dive on those you learn from. Look at their resume on LinkedIn. Do they really have the backgound they say they do? When I started, we had the financing thing down cold and we knew enough about construction to handle flips, but we needed deal finders. I found a parter that knew that, but lacked what I knew. Over the next 15-20 deals we learned from each other. That was my advice for getting started. I wish you well in your journey, Darrell. Let me know if you need to bounce ideas off of me.
I agree with Travis on focusing on the simple fundamentals. Buying right is probably the most important part of the whole process. Things like cash flow, location, renovation costs, reserves, and making sure the numbers still work even if things do not go perfectly.
That said, don’t force a deal just because you’re eager to get started. Being conservative is not a bad thing, especially in your first few deals. I actually think that mindset helps people avoid expensive mistakes.
At the same time though, there’s a difference between being careful and staying stuck in analysis paralysis. Most people never feel 100% ready before taking action. Someone once said something along the lines of “you’ll never feel ready because ready isn’t a feeling, it’s a decision,” and I think there’s a lot of truth to that.
The goal is not to eliminate all risk. It’s to educate yourself enough to make calculated decisions with confidence.
Always happy to connect!
Hey@Darrell Gibson check your messages on BiggerPockets. I sent you a link to a video of my response to this post. I used this post to create a video that I posted yesterday where I go in depth on your question that lots of new investors have which is "How do I know if a real estate property is a good deal."
Have you gone to meetups to network with other investors?
Have you gone to meetups to network with other investors?
I am going to one tonight. I found one here in South Bend for the North Central Indiana. Tonight's guest will talk about tax sales. I am super excited to meet some of the local folks.
Hi Darrell from Mishawaka, IN.
Congratulations, you have decided to invest in yourself and real estate and you have your grandparents, who had 20 rentals, and you would like to do the same.
Your questions is how to know if something is a good deal and how to find a trustworthy mentor.
Great questions. There are many deal calculators online to select from and YouTube videos to walk you through those calculators. Personally, I like things to be as simple as possible including those calculators. If you are focused on building a rental portfolio, you basically want market rents to be greater than all your monthly expenses including some reserves for vacancy and maintenance-consider starting with duplexes. I would also include the expense for an experienced property manager as they should be adding more value than they charge and make your investment as passive as possible.
As far as a mentor, look for an experienced investor or investor friendly Realtor with a teacher's heart in the areas you wish to invest. They are out there.
To Your Success!
Here is a cheat code, it's not easy but it's free and will definitely be worth it.
Find a professional RE investor, offer him an offer he can't refuse (something that takes very little time from him but gives him a huge reward and one he has skin in the game)
An example would be, if you help me analyze a deal and guide me on what to do I will give you X amount of equity.
Yes you are giving away equity but you are getting shortcut to years of experience, knowledge etc... Just make sure he is honest and trustworthy. This can speed things up 10x or more.
Hey yo! Long time listener first time caller.I’m 48 years old and tired of making other people money. My grandparents had about 20 rentals back in the day. Unfortunately, they were lost during the recession. I’m ready to move on and start my own adventure in renting. I’m struggling with how to analyze a property correctly. That has given me some analysis paralysis on taking the next step.
I guess what I’m asking is how do I know if a deal is good? How do I find a trustworthy mentor that doesn’t cost an arm and a leg?
Thank you for taking time to read. I look forward to hearing your guys advice.
Darrell
Real Estate Investor
I think the hard part early on is learning which assumptions you can trust. The math is usually simple, but rent, repairs, taxes, insurance, vacancy, and neighborhood quality are where a “good deal” can fall apart fast.
I was recently introduces to a gentleman that does DSCR loans.
@Darrell Gibson dm me, I run a local real estate group that does education, networking, etc here locally in the SB / MIshawaka area. I am a full-time investor and can help you get started.
Hey yo! Long time listener first time caller.I’m 48 years old and tired of making other people money. My grandparents had about 20 rentals back in the day. Unfortunately, they were lost during the recession. I’m ready to move on and start my own adventure in renting. I’m struggling with how to analyze a property correctly. That has given me some analysis paralysis on taking the next step.
I guess what I’m asking is how do I know if a deal is good? How do I find a trustworthy mentor that doesn’t cost an arm and a leg?
Thank you for taking time to read. I look forward to hearing your guys advice.
Darrell
Real Estate Investor
For South Bend, look up St. Joseph Realty Group - smart, informative and super professional.