Starting My Real Estate Portfolio

Chicago, Illinois
Chicago Real Estate Forum
5yFollow

Starting My Real Estate Portfolio

Ryan DiCanio
Aurora · Member since 2021 · 44 posts · 24 votes

Hey BiggerPockets community, I am looking to purchase my first duplex/triplex in the Naperville, Glendale Heights, and/or Downers Grove area. I am open to exploring other areas and will take any recommendations I can get! My budget cap is around $370k. I am willing to invest in a cheaper property that needs rehab work as well. 

I love connecting with others that share the same passion as I do and if you simply would want to connect to learn more about myself and my situation, feel free to reach out!

5Reply
34 views

Most Popular Reply

Tucker Cummings
Investor · Raleigh, NC · Member since 2019 · 433 posts · 743 votes
5y

My advice:

1) Acknowledge the seller's market, know that it's going to be tough to get good deals on the MLS. So open your funnel to off market deals.

2) People will always tell you its a good time to get in, a good time to get out, a good time to buy, a good time to sell, a good time to wait, a good time to act. Do what you want, just be smart and calculated about it.

3) Get educated. Ditch music, listen to podcasts. Ditch news feeds & social media (unless marketing) and start reading books and blogs about investing.

4) Try house hacking your first one. That's my biggest financial regret, that I didn't do this.

5) Acknowledge that you're going to mess up. It's part of the process and its the cost of your education by doing.

6) Just do it. Don't overthink stuff. You'll learn the most by doing.

8Reply
See this reply in the discussion

31 Replies

Jump to latestLatest
  • Edward Wodziak
    Investor · Woodridge, IL · Member since 2015 · 80 posts · 21 votes
    5y

    It's a bad timing, because it's a extremely a sellers market, where the buyers have to pay 10k over listing price, and buy as, and guarantee couple of 1000s over appraisal.   Naperville and Downers Grove is too expensive to cash flow for rentals.  Do you have realtor yet?  Also need pre-qualified letter from a lcouplep

    1Reply
  • Josh Mitchell
    Real Estate Agent · Naperville, IL · Member since 2013 · 402 posts · 177 votes
    5y

    @Ryan DiCanio awesome to hear you are ready to start your journey! Tough market right now, but dont let that get in your way! Continue to analyze and prepare so you can execute when the time comes. I’m happy to help any way I can. I am an agent who also invests in Naperville! 

    2Reply
  • Ryan DiCanio
    OP
    Aurora · Member since 2021 · 44 posts · 24 votes
    5y

    @Josh Mitchell Thank you for reaching out! I understand how tough the market is right now, but like you said I am not going to let that slow me down by any means. I am physically, mentally, and financially ready to seize an opportunity when it comes, but my initial question for you would be: What are some initial steps I can take right now other than running my analysis on certain properties?

    0Reply
  • Ryan DiCanio
    OP
    Aurora · Member since 2021 · 44 posts · 24 votes
    5y

    @Edward Wodziak Thanks for the feedback! I understand the market is tough right now, but I believe there are still opportunities to be seized based off what I have seen and what other connections have been able to accomplish. I do not have a realtor yet and not sure what pre-qualified letter you are referring to. Can you explain that?

    Have you owned rental properties in the Naperville and Downers Grove area before? Or is it based off what you seen and analyzed?

    0Reply
  • John Warren
    Real Estate Broker · 3412 S. Harlem Avenue Riverside, IL 60546 · Member since 2015 · 6k+ posts · 5k+ votes
    5y

    @Ryan DiCanio welcome to the community! This is a perfect time to get into the game because... you are ready to get into the game! Yes, the market is red, red hot, but real estate investing is a get rich slow game. Analyze quickly, and purchase slowly when it makes sense and you will be fine. 

    Others on here are correct that it can be challenging to get in right now. We listed three properties last week and all three ended up with multiple offers. On the buy side, we submitted 6-8 offers and all were involved in highest and best rounds. This is where having your team together makes all the difference! You just have to know how to work in this environment, but this will eventually change back to a buyer's market. Just stick to your criteria and look to buy great buildings in great areas like you are. 

    2Reply
  • Henry Lazerow
    Real Estate Agent · Chicago, IL · Member since 2017 · 2k+ posts · 2k+ votes
    5y

    Those areas have such high taxes its hard for deals to work when properly running the numbers. I would look into Elgin you can easily find a 3 or 4 unit there that actually cashflows or go into north side chicago/evanston where the rents are high enough that the properties positive cashflow when know market rents. Most deals you raise rents and buy under market so its good to research market rents or ask your realtor in each specific area.

    1Reply
  • Jonathan KlemmBusiness Member
    Moderator
    Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
    5y

    @Ryan DiCanio - Welcome to the BP community.  Sounds like you have a pretty sound plan in place.  As others have mentioned those areas are a little pricey, but I definitely like flipping in those areas.  Everything is selling so quickly.

    Happy to connect and see how we could

    [email protected]
    Quality Builders4.966 Reviews
    WebsiteView Page
    1Reply
  • Ryan DiCanio
    OP
    Aurora · Member since 2021 · 44 posts · 24 votes
    5y

    @John Warren Thank you! I really appreciate your feedback and support! I am looking to learn and maximize my opportunities in anyway that I can. I am looking to move out on my own as soon as possible, but understand it won't be a quick nor easy process with how the market is. Do you have an opinion on when you see the market changing?

    0Reply
  • Ryan DiCanio
    OP
    Aurora · Member since 2021 · 44 posts · 24 votes
    5y

    @Henry Lazerow thanks for your input! That seems to be the consensus that I have gained from the community. Do you have any locations I can look further into around the outer Chicago area? Not looking to live in the city, but also want to stay somewhat close to the suburbs for family!

    0Reply
  • Ryan DiCanio
    OP
    Aurora · Member since 2021 · 44 posts · 24 votes
    5y

    @Jonathan Klemm thanks for the warm welcome! I would love to connect further and learn more about yourself and the path we are both heading down.

    1Reply
  • Paul De Luca
    Real Estate Agent · Chicago, IL · Member since 2018 · 1k+ posts · 1k+ votes
    5y

    @Ryan DiCanio

    It depends on how far west you want to go. Are you looking to house hack? You'd have some options in Aurora and Elgin but if you want to stay in the near western suburbs/closer to the city I'd target Berwyn, Addison, and Bensenville. Berwyn has a lot of 2-4 unit inventory relative to other suburbs, especially those in DuPage County.

    1Reply
  • Ryan DiCanio
    OP
    Aurora · Member since 2021 · 44 posts · 24 votes
    5y

    @Paul De Luca Yes I am looking to house hack for a couple years! Those are all areas that I would be open to looking at. I would also already have one person moving in and renting from me as well no matter where I go (which is a plus). Would love to connect further if you're interested! 

    1Reply
  • Brandon Gore
    Rental Property Investor · Chicago, IL · Member since 2018 · 7 posts · 2 votes
    5y

    @Ryan Richard DiCanio

    Congrats on taking the first step in your new journey! Just as others mentioned it is a fast and hot market but don’t let that deter you because it’s only going up from here! You’ll be fine as long as you have a plan and knowledgeable people on your team. If you have questions, let’s connect!

    0Reply
  • Henry Lazerow
    Real Estate Agent · Chicago, IL · Member since 2017 · 2k+ posts · 2k+ votes
    5y

    Check out portage park/edges of belmont craigin and jefferson park, many of these areas have a suburbs feel and if you can afford a 4 unit can cashflow well. The second you step into suburbs you have way higher tax rates, but there thankfully are many areas within city limits with a suburban feel and good returns. 

    0Reply
  • John Warren
    Real Estate Broker · 3412 S. Harlem Avenue Riverside, IL 60546 · Member since 2015 · 6k+ posts · 5k+ votes
    5y

    @Ryan DiCanio the market is pretty red hot everywhere right now, so I wouldn't try to chase deal into areas you don't know. Instead, I would focus on areas you already want to live in and start to learn your local sub markets. We listed properties this past week in Stickney, Berwyn and in the Tri Taylor neighborhood, and all of them had 5-10 offers within a day. In this market, you want to be very sure of what you are buying as you will have to act very, very quickly. 

    0Reply
  • Tucker Cummings
    Investor · Raleigh, NC · Member since 2019 · 433 posts · 743 votes
    5y

    My advice:

    1) Acknowledge the seller's market, know that it's going to be tough to get good deals on the MLS. So open your funnel to off market deals.

    2) People will always tell you its a good time to get in, a good time to get out, a good time to buy, a good time to sell, a good time to wait, a good time to act. Do what you want, just be smart and calculated about it.

    3) Get educated. Ditch music, listen to podcasts. Ditch news feeds & social media (unless marketing) and start reading books and blogs about investing.

    4) Try house hacking your first one. That's my biggest financial regret, that I didn't do this.

    5) Acknowledge that you're going to mess up. It's part of the process and its the cost of your education by doing.

    6) Just do it. Don't overthink stuff. You'll learn the most by doing.

    8Reply
  • Ryan DiCanio
    OP
    Aurora · Member since 2021 · 44 posts · 24 votes
    5y

    @Brandon Gore Thanks for the support! I would love to connect further - I want to learn as much as I can from as many different people as I can. 

    0Reply
  • Ryan DiCanio
    OP
    Aurora · Member since 2021 · 44 posts · 24 votes
    5y
    Originally posted by @Henry Lazerow:

    I will look into these areas as well. You make a good point with the tax rates of the suburbs, as in my analysis' so far they are consistently higher than other areas. I would love to connect further if you're interested!

    0Reply
  • Ryan DiCanio
    OP
    Aurora · Member since 2021 · 44 posts · 24 votes
    5y
    Originally posted by @John Warren:

    @Ryan DiCanio the market is pretty red hot everywhere right now, so I wouldn't try to chase deal into areas you don't know. Instead, I would focus on areas you already want to live in and start to learn your local sub markets. We listed properties this past week in Stickney, Berwyn and in the Tri Taylor neighborhood, and all of them had 5-10 offers within a day. In this market, you want to be very sure of what you are buying as you will have to act very, very quickly. 

     I appreciate that tip John. Essentially become extremely knowledgable on where I want to live first, then start expanding once I have a strong knowledge base. 

    0Reply
  • Ryan DiCanio
    OP
    Aurora · Member since 2021 · 44 posts · 24 votes
    5y
    Originally posted by @Tucker Cummings:

    My advice:

    1) Acknowledge the seller's market, know that it's going to be tough to get good deals on the MLS. So open your funnel to off market deals.

    2) People will always tell you its a good time to get in, a good time to get out, a good time to buy, a good time to sell, a good time to wait, a good time to act. Do what you want, just be smart and calculated about it.

    3) Get educated. Ditch music, listen to podcasts. Ditch news feeds & social media (unless marketing) and start reading books and blogs about investing.

    4) Try house hacking your first one. That's my biggest financial regret, that I didn't do this.

    5) Acknowledge that you're going to mess up. It's part of the process and its the cost of your education by doing.

    6) Just do it. Don't overthink stuff. You'll learn the most by doing.

    Absolutely LOVE this advice Tucker! From a webinar I had been a part of, I feel that off-market is a great way to find a deal and can even work better in your favor if your a personable person. For off market properties, do owners still list their properties places or to find them I would have to drive around in my area? 

    I am definitely going to house hack for my first investment for a couple years. And I already am accepting of the fact that I will mess up. That has proven the best form of education in my lifetime so I am not afraid of any bumps in the road along my journey.

    Thanks again for the tips! Lets connect and discuss further if you'd like.

    1Reply
  • Account Closed
    Rental Property Investor · FL · Member since 2017 · 74 posts · 27 votes
    5y

    @Ryan DiCanio

    Love it! Are you using a realtor at all? Or what are your criteria for finding the buildings? Ever considered turn key?

    0Reply
  • Ryan DiCanio
    OP
    Aurora · Member since 2021 · 44 posts · 24 votes
    5y

    @Account Closed currently in search for an educated realtor, do not have one yet. I am currently looking for properties on my own until I can find one. To be honest, I was just introduced to the turn key concept the other day! I have a limited knowledge base on the subject; have you had success with it?

    0Reply
  • Tucker Cummings
    Investor · Raleigh, NC · Member since 2019 · 433 posts · 743 votes
    5y

    @Ryan DiCanio several ways you can find off market deals. Connect with other wholesalers and investors, you can drive for dollars, send direct mail, make cold calls, build a website and drive traffic through SEO and paid advertising, etc. The only marketing forms I advise against are bandit signs, ringless voicemail (rvm) and text blasting (sms). It just comes off as super spammy and can build a bad brand name, plus bandit signs are basically advertising by littering. 

    Good luck!

    1Reply
  • Ryan DiCanio
    OP
    Aurora · Member since 2021 · 44 posts · 24 votes
    5y

    @Tucker Cummings all great information Tucker, thanks for the help! I will put some of those into action today.

    0Reply
  • Account Closed
    Rental Property Investor · FL · Member since 2017 · 74 posts · 27 votes
    5y

    @Ryan DiCanio

    I have used them for everything. Pros and cons of course but from a truly hands off stand point and having a professional PM in place certainly helps.

    0Reply
Join the conversationCreate a free account to reply, vote on answers and follow this thread.
Log InJoin for Free