The safest bet is to get yourself some oil based primer and a coat of paint on the interior when turning it over.

If you are able to self promote on social media, that might be your best bet.

So I think my best bet to start off with is to find a property management company.That said, I’m wondering if anyone has tips on property management companies they would recommend, and/or any tips on how to find the best property management.

I am also willing to bet you dinner somewhere that the loan docs on the underlying mortgage have somekind of prohibition on doing exactly what is being done. 

Nest seems like a good bet, but it's not clear if they are compatible...?

I'm giving my mortgage lender the money early, so I'm skipping the corresponding interest payments ($917.94 + $916.25 + $914.56, etc. in that middle column there), which saves me tens of thousands of dollars.

Your best bet is hire a local designer. 

Local banks who don't re-sell these are typically your best bet, they like relationships.  

The best bet for that would be getting an awesome property manager that does basically everything aside from supplying the financing for the home. 

I am a tax attorney and i still am confused, and I am willing to bet that most people will be putting it on schedul e, not paying se tax, not calling it passive, and deducting losses against w2 income, and playing roulette with audits.