Like anything it has to stay balanced but small gestures go a long way in reducing turnover and mitigating many "would be" issues. 

I know I know getting property won't be an issue, I've done it once and that experience helped me so much, but what if i wanted to acquire two properties this year?

You would expect a clean title at close so if there is some issue, then either it would be resolved by the seller or the deal would fall through.

Purchasing a STR in a somewhat sketch area is a terrible idea and as others have mentioned, is going to open you up to potential issues. 

Title issues tend to be the fact pattern where properties are truly not financeable but that's rarely the case when you see the "cash only" adverts.Ultimately, proceeds will be transferred through a title company and its not as if the buyer is showing up with a duffel bag filled with cash.

This is one of the biggest insulation issues second only to the attic.

Customer Service integration to handle tenant issues, monitoring of Mechanical issues where the A.I. can proactively do something to ensure it's well maintained or to be able to fix an issue, etc.My Portfolio has basically been self-running except for occasional P.M. 

The moisture issue and structural issue need to be addressed and you can do so before the insurance adjuster comes out.

There is no issue with eviction for non-payment of rent during the winter in Wisconsin.

The foundation was already approved, permitted and finaled years ago for a 3400 sf house, and its solid and I won't be building directly on the overhang edge; but rather back away from the edge a few feet to prevent any load issues all the weight will be on the longer sides of the existing footing.