I have been in the real estate world for about 2 years now working with a property management team and running my own interior design business for STR.

Who is making the design choices and who has the experience.   

My phone goes on DND after 9PM and only people I designate will ring through.I had a leak at a house one time and when they couldn't get me they called the fire department who came and shut the water off at the house.

Whether that’s price, location, interior, or a combo of all I don’t know, but either way it’s only as good as the historical data and methodology. 

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?!

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.