One thing I’ve noticed about real estate investing is that knowing when to walk away from a deal can be just as important as knowing when to buy. A property might look like a great opportunity, but once you factor in repair costs, holding expenses, financing, and potential surprises, the numbers ...
I have a 3 bedroom unit with 3 adult and from time to time, they have 2 toddlers that stay for a short period of time from time to time They also have 2 teenagers that does does the same thing what would be the best way to handle this
I am new owner of 12 units property (2 buildings). This is my first winter season so need an advice from experienced investors and property managers. What all things I should take care of before winter starts in Chicago? I have two boiler rooms. What all things I need to do around boilers and the...
What is the biggest challenge you’re facing in your investment journey, and what stage are you currently at? This post is simply intended to offer support and help. 🤝
For those of you who own 2–4 unit properties in Chicago, I'm curious what your long-term strategy looks like. Are you holding onto your properties for rental income, considering selling while there's still buyer demand, or looking to leverage your equity into a larger investment? As someone invol...
I’ve been thinking about how many real estate agents come across buyers and investors who find the right property but struggle to secure the financing needed to move forward. Sometimes it’s not that the buyer doesn’t qualify for anything. They just haven’t explored all their funding options. I wo...
Hey everyone! I’m hosting our monthly Pilsen Real Estate Meetup on Wednesday, October 28, and would love to meet some fellow BiggerPockets members. It’s a casual gathering for investors, house hackers, future buyers, and anyone curious about Chicago real estate. Come talk deals, financing, renova...
Monthly real estate meetup in Pilsen (Chicago) — casual, free, open to investors, house hackers, future buyers, and anyone curious about the local market. Good mix of local agents, investors, contractors, lenders, and other industry folks. Come talk deals, financing, renovations, and what's actua...
Im looking at a 2-story, ~3000sq ft mixed-use building (wood-frame with brick exterior, ground-floor retail + two residential units above, unfinished basement, small 2 car garage) in the Chicago area built in 1910. I will be inspected and it looks to be in average shape. When does building age be...
Looking for any recommendations on DSCR Loans that will for sure close. Looks like a lot of feedback says they are approved only to not close in the end. Thanks in advance!
Getting close to call for CO on a multi-unit gut rehab and realized that I neglected to use 1 hr fire rated doors for unit entry doors. Just used regular steel entry doors. Is this something that's going to 100% get flagged and need to be rectified? Is there any work around? I've already trimmed ...
Hello, RE friends! Wanted to see if anyone has insight into the best long term cash out refinance programs right now? Best rate? Highest LTV? Lowest fees? I’m refinancing 2 BRRRR rehabs in Illinois. Thanks!!
Hello, I am looking into building a 4 unit new construction with the VA loan ( IN CHICAGO). Has anyone done one on a multifamily? Pros and cons? Let me know vs just me just buying an existing 3-4 units with the VA loan.
I’ve been interested in connecting with more real estate agents who work with investors, particularly those involved in fix-and-flip projects, rental properties, and investment opportunities. One thing I’ve noticed in the business funding space is that sometimes investors find great opportunities...
I've spent the last several years on the marketing side of real estate investing, working with a cash home buying operation here in the Northwest Indiana / Chicago Southland market (Lake, Porter, LaPorte, Jasper, and Newton counties, for those who know the area). Before that, I spent about 16 yea...
Hello, I have a small multifam of 4 units. I inherited some washer and dryers from old landlord, I want to set up a coin operated system. I don’t want to retrofit the machines themselves, is there coin operated outlets where it can time the washers dryers? Should I even put a coin operated laundr...
👉 Reserve your spot for Oct 17 (Chicago IL): https://site.cfbcinvestor.com/chicago 📍 Not in Chicago? Find the Cash-Flow Breakfast Club nearest you: https://site.cfbcinvestor.com/find-your-club ⭐ 1,250+ five-star reviews • 18,479+ members nationwide • 50–100 investors in the room each month • All ...
I have a 100 year old two flat in a great neighborhood. I'm looking to do some renovations inside & out. I have scope, budget and a clue. I have been my own GC many times. This one is too large for me to handle. Yet all the contractors want to take me for a ride. Promise me one thing and then wor...
I’m interested in purchasing an investment property in Calumet City, Illinois. The property is a three-bedroom, one-bathroom single-family home that appears to need only minor repairs. It is currently occupied by a Section 8 tenant, and according to the owner, the property is up to code. The owne...
Hi BiggerPockets Community! I wanted to introduce myself to the network. I am a dedicated property manager with over 8 years of hands-on experience maximizing ROI for landlords across the North, South, East, and West sides of Chicago. Having personally managed an extensive portfolio of doors—span...
Three times a year, we do a Real Estate Investment Summit and this is our last one of the year. If you are looking for the motivation to buy your first deal or want to scale from what you are already have, this is the Chicagoland event for you. Date: Saturday, October 17, 2026, 12:00 PM to 3:00 P...
Hi Everyone. Can anyone recommend any good lenders who specialize in DSCR loans here in Illinois?
The garden unit is the most underrated space in a Chicago two flat. For anyone outside Chicago, a two flat is what most of the country calls a duplex, and the garden unit is the lower level apartment that sits partly below grade. Here is what I keep running into. The lower unit gets treated two d...
Looking for any recommended contractor that could help with a project in the Avondale/Logan Square neighborhood of Chicago. Full interior gut rehab of a 2-flat. Would very much appreciate any recommendations.
Looking for Rehab-Only Financing Advice I’m currently under contract on a single-family fix-and-flip in the Chicago area. I’m purchasing the property with cash, so I don’t need acquisition financing. What I’m looking for is a lender that will finance only the renovation costs after closing. I fou...