I would recommend targeting 30 day minimum rentals (Most associations are 90+), allowing 12+ rentals per year (most allow 1-3), and no in-person screening for tenants required.

And you can't legally dictate how much they carry for personal belongings. 

Being a curious person, I gained an interest in real estate investing due to other classmates being interested in real estate.

i'd pick a market close by, or that you have a personal connection to, or that you visit often.chasing cash flow by itself can lead to negative outcomes - for example, these investors bought in supposed "cash flow" markets:https://www.biggerpockets.com/forums/12/topics/1215726-break...https://www.biggerpockets.com/forums/963/topics/1195280-expe...https://www.biggerpockets.com/forums/48/topics/1137397-balti...hope this helps.

Quote from @Matt Cook: I would really get with a realtor that is in the area of that property and that sells a lot of homes to comp the property on what it can sell for after the remodel.

I havent worked with him personally but have received a good referral for him.

Also interested in networking to learn more about my personal interest in STR's primarily in the Tampa, Bradenton, and Sarasota markets along with other southeast coastal and mountain markets. 

Quote from @Michael Challenger: I have no qualms with hard money lending, but I need to learn more about the process and structure to these for typical deals so that I am more comfortable and in a position to reduce my personal risk and risk to investors as much as possible.

And this means you're going to spend some money on that person.

I've never done one personally but my understanding is it involves the home being put into a trust, with the sub2 purchaser buying the trust from you.