New Chicago Investor Looking to be a First Time Homeowner
Hi All,
My name is TJ and I have been working and living in Chicago for the past 4 years. After years of renting, my spouse and I have decided we want to make the leap into real estate investing. Our goal is to find a 2-3 unit property with the plan to house hack. I have been searching for the right property with my agent for about a month or two. So far we put in one offer, we were unfortunately (maybe) outbid on. The house seemed to be structurally sound, just needed cosmetic updates for the most part (we planned to have an inspector come out regardless if not) and the numbers seemed to work on paper.
My takeaway from that first offer was that I felt very overwhelmed by the unknown after we submitted. I was only able to see the house once and the only documents I received from my lender at the time was my pre-approval letter which did not have much information. The numbers looked right on the template my agent and I have been using but after thinking on it - a lot of the numbers were just estimates. I know this comes with time, but just curious if anyone has advice on how to be as prepared/informed as I can whenever we put in that next offer. Should I be receiving more detailed information from my lender? Anything I might be looking over or past mistakes others have made that I can learn from? Appreciate any help!
Most Popular Reply
What's up's TJ @Anthony Pomponi! Fantastic to hear that you decided to switch from renting to owning it really is the true path to growing your net worth!
I love the idea of looking for a 2-3 unit Chicago property. I personally think you'll have better luck looking for a 2 unit because if you are thinking about going with a low down payment (FHA or 5% conventional) then you won't have to go up against the self-sufficiency test, which basically requires your rent to cover 75% of your principal, interest, taxes and insurance including the unit you'd stay in.
Just curious how did you connect with your current agent and lender? Jus tasking because your lender and agent should be showering you with information and if they arent maybe you want to find some a bit more geared toward investors/multifamily buyers.
Happy to link you up with some trusted folks!
- Jonathan Klemm
- [email protected]



