(There's a continuum, I get it - but hopefully the sentiment lands.)Of your "questions" at the end of your post, I think your first outcome (1.) is probably the most likely and I would begin preparing for that eventuality (i.e. engage a L/T attorney, procuring cash reserves for non-payment during eviction, funds for extensive renovation). 

I want to be able to eventually have a property that I can give to each of my kids when they graduate high school as well as possibly be able to assist other single fathers that are going through what I was with my divorce and having a difficult time finding a place to live.

All-in basis: ~$65,000Estimated retail value: ~$110,000Rented for ~$1,000/month for two yearsTenant eventually purchased at a price we were happy withProceeds were rolled into a better property via 1031 exchangeLessons learned?

I don’t believe most “clawbacks” are due until you eventually sell the property you 1031’d in to.

Zoning & ADU ConsiderationsChicago’s ADU Ordinance applies if you create an additional dwelling unit beyond the existing count.If you stay at 2 units total (just shifting one unit partially to the basement), you likely don’t trigger ADU rules—but confirm with zoning since each ward can interpret things differently.If you want to eventually rent the basement as its own apartment, you will need proper zoning, permits, and a second exit per Chicago code.3.

Sure enough, the city eventually annexed the park, and overnight the property taxes quadrupled while the schools went from some of the best in the county to some of the worst in the city.

Any real-world input on that would be super helpful.The idea is to eventually run this new build as an Airbnb.

Many property owners who carry back financing eventually wonder if it’s better to sell the note or keep it for cash flow.

Not the biggest Dave Ramsey fan, but I do believe in 'live like no one else so eventually you can live like no one else"While I have owned a home since my early 20's, I never had the dream home but more like shelter. 

I’ve spent the last 10+ years working hands-on in new home construction, remodeling, and residential project management.Recently, I launched Roman Property Developments (RPD) with the goal of transitioning into investing—starting with wholesaling off-market deals and eventually growing into new development projects.I know I’ve got a lot to learn on the investing side, but I also believe my construction background gives me a leg up when it comes to evaluating properties, estimating repairs, and seeing the potential in undervalued deals.Looking to connect with other investors, buyers, and pros here in Michigan.