I d hate to be audited and come under penalties because I answered yes to questions above.There are advantages to paying some SE tax and filing a schedule C.

I am seriously considering doing exactly this in SE Texas.

“Getting into real estate” per se is not your goal.

Jeff, I don't have any industry experience, but can give you consumer feedback.I live in SE WI and many national carwash companies have come into the market and built some very high end facilities. 

And of course you would have to have a  buyer that values it higher for a sell to work.But I totally agree just because it is an STR does not make it worth more per se.

Try to figure out what will work best LONG term for you...and do a bunch of that, so it's scalable.I've continually created more headaches here in Chicago by doing STR, MTR, LTR, wholesaling flipping, etc....not I'm laser-focused on our renovation business but have enough expertise across the board to share what didn't work for me lolI am no longer investing, but I love Garfield Park and anything SE towards the lake. 

I don't have a mentor, per se, but I've got several folks who are many steps ahead of me that I'm learning from, who are kind enough to help educate me. 

I'm not an expert per se but know better.

He wasn't super interested in the deal per SE (as in the property or project).Some details:He only liked debt structureHe asked for a short list of investors who we'd borrowed money from.

Might be worth reviewing to hopefully learn from my errors https://www.biggerpockets.com/blog/2015-02-04-confessions-se...