I'd also learn a lot about maintenance and managing tenants.Then, with my hands-on experience, I could decide if I wanted to repeat the process or target 5+ units - which my experience would help with lenders.Good luck with whatever you decide to do!

How does this affect the feasibility of managing fixer-uppers or multifamily properties?

Chicago’s unpredictable weather can sometimes affect project schedules, so it’s essential to set estimated start and completion dates.

Try some broken record techniques repeating, rephrasing, etc. 

In Washington State, there’s often a distinction between short-term guests and tenants, but repeated and continuous occupancy can blur those lines.

Tax impacts include deferred gains, adjusted cost basis affecting future depreciation, and strict adherence to IRS timelines.

Some investors like having each property in its own LLC to limit risk, like if something happens with one property, it doesn’t affect the others.That said, managing multiple LLCs can be a hassle and add costs, especially with only a few doors.

The lender has told me that as the guarantor on the company this would still affect me personally so it's not much different at this point if we purchase under me personally or under the entity.

The discussions we see repeated today differ from four years ago because the market has changed. 

It is very unlikely that you'll have problems/be investigated for just one instance, but repeatedly doing this will absolutely raise red flags these days.