@Chris Utter If your issues are you don't want to drive and you do not want her knowing your address then just get a PO box from your local post office.

HUD would consider an office or living room as a bedroom for occupancy purposes per the Keating Memo.

There is a church for sale with 2 bathrooms, office and 2 class rooms.

If there are some busier agents in your office you can ask them too.

@Deniqua AntoineYour profile mentions that you are a realtor + househacking.If you are a realtor, you want to have a conversation to see if you are eligible for Real Estate Professonal Status(REPS).Below is a sample of expenses that realtor's are eligible to deduct - MLS Fees, Home office, Mileage, Business Gifts, etcHouse hacking makes your tax situation more complex.You purchased a property that is treated as both an investment property and a personal residence.

You may need to bump your scores, but most loan officers have the tools just as I do to help get your scores up.

.● Robocalls to emergency services, hospitals, doctor’s offices, healthcare facilities are prohibited.● Any calls made to lines for which the recipient is charged for the call are prohibited.● No artificial voices or recorded calls can be made to residences without the recipient giving prior consent (opting-in).

We are looking for a 4 bedroom (or 3+office) and 2.5 bathroom home, with a full basement.

@Jonathan Klemm, to answer your question my next steps from now until December 2022 is to bulk up my savings (my goal is to have 50-60k liquid to begin my search), research neighborhoods actively (I have a tentative list but sine I am originally from NY I'm still learning, research which folks  I want in my team (investor friendly loan officers, real estate agents, etc.), keep working at deal analysis so by the time I'm ready to buy I can run my numbers, and finally explore other options to investing in Chicago.

For me, the most common thing I've seen has been loan officers who are unwilling to admit they have no idea what they're doing when it comes to VA loans.