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.

I believe she lost the drive or desire to own a c- class property and is more interested in putting her design ideas into flipping homes. 

He may have renovated the units but all the mechanical systems are the same. 

i actually did that before i read the new messages in the thread, so it might not have everything you said in it. but let me read your post fully and see if i can understand, and try to make it happen.im using home designer 2022. you cant save anything with the free version.im thinking i might not need the island anymore.

The PDF version is designed to print and fill out by hand.

Just get a good cleaner and handyperson and keep up on the maintenance of the mechanicals (furnace, water heater etc) and you will reduce problems tremendously.