I think tax benefits should be secondary to buying something that would work well as a STR.I would recommend you consult a tax professional to see what possible tax benefits you could receive from buying this STR.

I've done this with my properties because I'm well known in my small town and don't want people to know what I own.

It's that simple.Doesn't hurt to have real hardwood floors and A/C as well.

I currently use Wells Fargo and it’s a pain in the butt to keep going there in person and setting up a security deposit account.

We do well with ours in Denver and Colorado Springs, for instance.

I've done a lot of value add as well so that helped speed up the process.

Exposed wire are a safety hazard and if they where missed by inspection  you may be able to complain as well.

I invest here as well.

Well, you can buy little portable washing machines that hook up to your sink- not unlike those freestanding dishwashers.

I understand where you are coming from as we always did our taxes on turbo tax as well until we purchased rental properties.