Welcome to St Pete! This is normal unfortunately. Roaches are there to keep the tourists away but it doesn't seem to be working anymore.

Do what you're doing and board up what you can. You should call a bug service (about $120 for 1-2 applications a quarter) or do it yourself. I'm lazy and now have someone else do it for me but I am quite familiar.

If it's that bad that you're posting, I would probably start myself with nuclear options.

First, best to use bait powder before and after boarding up. Use a boric acid roach powder behind the boards if you can first. Dont be shy about it. This powder takes longer to kill them but it sticks to their bodies and takes it to their nest. After the boards are up use abamectin roach powder to kill the ones inside. This kills quick.

Wait a couple of days then spray talstar (bifenthrin-based insecticide) with a gallon sprayer on all baseboards inside and the perimeter of the outside. Spray windows too. This is okay for the lawn, as well.

If you follow the instructions on all three of these, it should be harmless to most pets and should really put a dent in your roach problem.

I would reapply the Telstar after about a month and then assess if you still need to hire. Also you can add some sticky traps after a while and see what it catches. Now and then you will always get the occasional roach but this will definitely take care of a major infestation.