I’m also looking at another property under $150k for STR, you won’t find that in Tremont but Clark-Fulton close to metro, border of Ohio City and Tremont would be a good bet.

My salary is nothing crazy so there is only so much to offset.I think my best bet might be to hire it out.  

I am betting there is a lot of people happy to pay $100/$200 to do such, happy to be in a group, to go over the basics like *sole proprietor, LLC or S-corp for landlords, what is best for tax's and why.

After a thorough set up with them we simply email them receipts with a note for what it was for/what project and they allocate it into the right category.Now if you have the capacity to learn quickbooks or employ someone who is versed in it then that is your best bet. 

They do NOT have any web portals to be able to monitor or service your loan.

Be careful to not get your credit score lowered because you have too many inquiries.If you can't go conventional, then DSCR is your next best bet. 

@James RobertSo basically, its just betting whether the property will appreciate more or less than what you can do/invest with the cash proceeds?

At the end of the day it's a straight math calculation, and making an informed bet, but there are also a TON of nuanced reasons that finding a deal is difficult. 

Networking with some local investors/contractors in the area who may have experience or knowledge in this area might be the best bet. 

Not a confluence of factors I would bet my money on.