Just google the following: - special assessment - zombie condos - Florida condos (look for recent news)Since you are not living near the properties anyways, why not look in a landlord friendly state where the purchase prices are lower?

On the flip side, if you've got a bunch of Section 8 tenants living in a building that's in a neighborhood where a lot of the tenant base has good jobs, high credit scores, and are generally reliable people, you've got the most risky tenants in that tenant base and that ain't what ya want.

I live in Sheboygan Falls, WI. 

I live on the west side of London and would be happy to connect and learn more about your goals and see what I can do to help. 

At minimum, stage the living room and primary bedroom to give it some warmth.That said, have you thought about cutting bait and putting your money into a market where the numbers actually work?

Ideally we would love to live in my childhood home.

I live in the Milwaukee area and want to get started investing locally but eventually want to branch out into other cities and states.

In my area these are rare so they are difficult to set market rent, and I imagine get a lot of wear and tear with a lot of occupants living there. 

Furthermore, it aligns with the growing trend of home improvements that enhance daily living while maximizing investment returns.

For scaling your portfolio, consider house hacking another multi-family property to minimize living expenses while building equity.