What apps are best for finding the most hilly roundtrip rucking or running route near my home?

There is damn little elevation change in the state of FL

This sucks - because unless you are between Lake City and Panama City, you'll never find a legit incline that any normal human would call a "hill", and even those are pretty anemic.

My recommendation would be to either hit the gym and use stair-steppers, or find a local business or public building (hospital??) that you can permission to go up and down the stairs. I really apologize, but outside of putting on crap tennis shoes (sneakers) and walking in 6-12" of water on the coast, that's all I've got.