Hello BP Fam, I am looking for a tax strategist/CPA. Me and my husbands tax facts have gotten more complex this year and we are interested in strategies and advice to lower our tax liability for the upcoming years. We have 3 properties, one SFH, and 2 duplexes. 2 properties is owned in our person...
Hi BP community, I'm Whitney, a Chicago-based business owner and first-time commercial developer. I've spent the last 8 years as a hairstylist and salon owner, currently operating Cutting Club Chicago across two locations in River North and Avondale. Building and running a service business across...
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...
One thing I’ve noticed about short-term rental investing is that purchasing the property is only part of the financial picture. Between furnishing, renovations, maintenance, unexpected repairs, and seasonal fluctuations in bookings, having access to additional capital can make a big difference. I...
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...
Hello, as I'm just getting started in Wholesales I've been trying out a couple different dialers and CRMs. I tried Mojo Dialer for a little while then switched to Flipster however I'm haveing ongoing issues with the dialer provider they use Aircall. I would love to hear what software you guys are...
One thing I’ve noticed is that finding a profitable business to purchase is one challenge, but getting the financing together can be a completely different story. A lot of entrepreneurs don’t realize how many business funding options are available or how much their business structure can affect t...
Hi all, I am a house hacker with 2 buildings, 7 units on the north side of Chicago. House hacking has been a great way to get my feet wet with investing. For the past year I have been exploring different strategies for investing BRRRR, Fix & Flips, and even house hacking again. I've made connecti...
I am a mortgage lender and have a client that would like to refinance her home into her own name due to a divorce. She is a nonprofit business as a midwife, but operates under a private ministerial association. She does not file taxes. She does not get a W-2, 1099, or 501 C3. Who can lend for her?
I have about 80k in equity in a condo and wondered if it is enough to get started on a flip. I would need to sell my current home and rent for the time being but I would have 70k cash.
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 have about 8 doors (mixed of SFH and multi-units) spread throughout Illinois. I don't like how my current insurance company dealt with the storms. I'm exploring other options. Any recommendations?
Property management involves much more than collecting rent and finding tenants. From handling maintenance requests to communicating with tenants and managing daily operations, there’s a lot to keep track of. I’d love to hear from those working in property management: What takes up most of your t...
Hi how are you doing BP community I have a loan of one of my rental properties with rocket mortgage and they are offering dscr to cash out refi and I wonder if anyone worked before with rocket mortgage they offer $0 out of pocket fee , thanks
I've been working on a refinance for a BRRRR in Indiana with a broker for the past couple months. I had the ARV estimated at $130k, with a loan amount of $97.5k. I had my rate locked at 7.375%. I got a call from the broker today that we need to go with a different lender because he had apparently...
Do you update your lease annually? The Chicago Association of Realtors releases a new lease at the beginning of each year which ensures the lease is in compliance with new legislation. The 2026 Lease had several updates including the requirement of a Safe Home disclosure as the first pages of a l...
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...
Hello, I am short 40k for my next deal. I have 2 options to access cash. Option 1- Sell a vacant lot in SW Florida that was purchased in 2022 at a premium. It’s value has dipped and is not going up any time in the near future. Consistently receiving offers for 10k less than what I paid (a 20% los...
I am looking for some recommendations for an inspector for multi family in Chicago. Thanks!!
A Tax Benefit Twist on Cost Segregation I’m sharing this because it may give another rental property owner a tax question worth asking. Five roof replacements resulted in a $9,102 tax deduction for our rental portfolio. And the deduction had nothing to do with depreciating the new roofs. The new ...
Hello BP community I am undercontract for a triplex in east garfield park, 5min walk to Kedzie-homan line. I am wondering if I should rent out one unit as furnished mid or short term rental or even by room for medical students/travel nurses/travel techs. I know the area is poor in terms of amenit...
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...
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!
I’ve noticed that one of the biggest challenges contractors face isn’t finding work. It’s having enough working capital to take on more projects. Between purchasing materials, paying employees, renting equipment, and waiting for customers to pay invoices, even a profitable contracting business ca...
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 ...