Depending on which company you engage with, make sure whatever you order can be delivered.

Having a great team behind you is a good cure for that.They will hold you accountable and let you know if it is a good deal and not to pass it up or if you are being completely sane and it is not the right deal.I look forward to seeing you engage in the community further and level up as an investor!

I would research what happens at the end of a balloon mortgage thoroughly before engaging this deal and make sure you feel comfortable with it.

I do really enjoy the hospitality aspect of STR and I do interior design for work, so the thought of furnishing for use buy others is enjoyable to me....What would you do in the current climate?!

Based on your description of the deal, you need to engage an SEC attorney who can set up an appropriate structure. 

I currently have both STRs and LTRs.I would recommend investing in Ybor, Seminole / Riverside Heights, Midtown or South Tampa.I have personally owned, designed, renovated and re-sold 16 homes in Tampa in the last 3 years.

In a crowded market like Orlando the recipe for success is simple, Focus on the client experience and that begins with cleanliness; Have a well-designed and themed house (you don't have to go crazy but try to be unique); Have Amenities to offer, there are a bunch of communities and the amenities they offer are powerful marketing!

To demonstrate my technical competence, for my personal house I built a steam shower, installed radiant barriers with rock wool, and a wood stove insert with bathroom radiant heated floors and re-designed radiant floor heat zones, cutting winter energy consumption to 1/8, installed a whole house fan cutting summer energy to 1/2, extensive localized landscaping leading to a reduction to 1/8 the yard work, plus random quality of life improvements like wifi switches, heated floors and toilet seats, skylight install, exposed structural beams, and master bedroom laundry including electrical and plumbing, cathedral ceilings with skylights, a steam shower with wifi controllable lighting and music, concrete countertops, etc. 

As has been alluded to before, I would partner or at least get extensive advice from experiend developers or engineering firms that have designed subdivisions.

I'm not real familiar with Stessa, but I know there are programs designed to manage rentals (Innago, TenantCloud, RentTec Direct, etc) that are free or cheap to use and they can help track tenants, leases, expenses, maintenance, and more.