Sounds like I am going to have to do some further research on how to investigate past evictions since it seems there's no catch-all approach.

Two, (not mutually exclusive) approach’s.  

I’m curious, when you’re entering a new market, what’s your approach to starting those in-person connections?

Long story short.. they inflated rent projections, sliced corners on property management, and almost left him holding the bag when the actual numbers came in.Vetting a syndicate means getting cozy with the sponsor’s track record, verifying their underwriting approach, and understanding whether they’ve handled rough waters before.

I would at least start there and good timing to figure out a plan with spring slowly approaching and our busier sales season in WI.  

I also notice that @Gregory Schwartz mentioned Huntsville in particular—I definitely think that it’s a strong market for long-term appreciation.As for your concerns about investing out of state, I think an investment strategy that is as close to passive as possible would be best.A do-it-yourself approach—where you acquire a property, place a tenant, interview a bunch of property managers, and handle maintenance yourself—is going to be pretty tough to do remotely.

For average investors without large amounts of capital to deploy this is a common approach to growing a portfolio.

There're some alternative planning approaches, but they are always case-by-case.  

I am curious enough to try different approaches and find out what worms best.

That kind of restriction just doesn’t work for someone like me.I’m trying to figure out if I might be missing something in how I’m approaching this or if others have insights or examples of towns that not only allow STRs but also have laws that offer enough flexibility to operate in the way I’m aiming for.Many towns technically permit STRs but impose restrictive rules like membership requirements, ownership duration limits, or rental day caps, making operations challenging.