Splitting the gift across multiple years may reduce immediate tax reporting but requires appraisals, legal documentation and proper structuring.If the house is highly appreciated, holding it for inheritance may be more tax-efficient because the recipient would receive a stepped-up basis to the FMV at the time of your passing, eliminating much of the capital gains tax liability.This post does not create a CPA-Client relationship.

I focus heavily on the sell side and on the buy side only work with high net worth individuals so the newbie wanting a 400k multifamily with an FHA loan probably isn't for me. 

With a 7% interest rate and high HOA fees, the key is evaluating if your skills and investments can generate higher returns elsewhere.

Also, providing value to others at a high level will pay off for you in the end if you stick with it.

Highly suggest coming out to some of the local chicago IN-PERSON meetups! 

Sounds like you need to have a relationship with a couple of good contractors, 40k for vinyl siding sounds high, what was the material cost.  

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

However, there's a critical detail that many tax advisors conveniently overlook when promoting these studies.Here's the uncomfortable truth: If you're a high-income earner (AGI > $150,000) and not actively managing your properties, those promised tax savings might be locked away for years.

When investing in high cash-flow markets, I always recommend working with an investor friendly agent so you're able to gain the right insight on the different areas and the risks involved.

Thats very highly unlikely.