Water and sewage main laterals are all at the street running perpendicular to the lots, Power/Internet lines as well. 

Roof trusses cross perpendicular over the wall ....it's likley load baring. .

Also, I don't know the formation of your driveway and garages, but I have maximized my parking by actually blocking to garages with three cars parked perpendicularly and then renting the garages for storage.

I can see where you are coming from regarding weight bearing but, most weight bearing walls on a standard home are close to center or perpendicular wall intersections making in impractical in some cases. 

I believe that Florida code requires that they be anchored perpendicular through the window frame channels and into the casements if the existing frames weren't impact rated, but check with the Hillsborough County building dept. to be sure.

Is the strip center parallel or perpendicular to the road?

The flooring would run perpendicular to the floor in the rest of the house.

The street perpendicular to one side is $1M+ homes, but the next street isn't great, probably $200k-ish.

If we put a 4’ bathtub perpendicular to where it is now, we’ll have about 2 feet of dead space between the wall and tub because of the sloped ceiling and the window. 

While reviewing the original plat it looks like the property lines should be perpendicular to each other while on the survey they are not also on the plat it is recorded the distance between the two properties across the street from each other should be 55ft if I measure from one fence to the other fence it is pretty dead on could the survey be wrong?