What states/cities make the most sense right now? 

Battery Park City Exchange (New York City): The city of New York engaged in a land swap with the Battery Park City Authority, allowing for the creation of a new public school and affordable housing units in exchange for a parcel of land that was then developed into a high-value commercial property. 5.

Hey @Keagan Scott, so I don't have any insight into Gary, IN but here is a blurb -"Those looking to rent out their properties for less than 30 days (about 4 and a half weeks) will have to get a permit, pay a one-time $150 fee, and have a city business license.

For projects with 150 or fewer units, the city has 60 days for eligibility review and 90 days for final approval, including design review.

I do not worry much about "hurried or sloppy work" because it is also in my contract that all work must pass inspection, which may include the city / county (for permitted projects), lender and myself.

Midwest cities with populations under 300,000 typically have cheap property taxes.

If you’re set on Florida, focus on areas just outside the main city that are still growing—you’ll find better deals there.

Also had to replace fuse panels to make it work - going back and forth with the city was dificult.

Conversely, a new built A class SFR, in A class market of significant growth via a well laid out planned city development, great schools, area people are glamouring to move to, a-class tenants, very very low risk.

Since you’re considering Midwest markets, I’d highly recommend adding Detroit to your list of cities to research.