Does he have an attic? Get as much wire up there as possible. 3 dedicated dipoles for 40m, 20m and a 20, 17, 15, 12, 10 combo then a fourth with as much wire as he can afford to string up. As long as it's 100 watts or less and he takes proper safety and mounting precautions then all should be good.

Then look at a random vertical that runs up a tree, over the top and terminates halfway down the other side. Mount balun at base and feed there, bury coax after treating jacket with a weather proofing coating that stays on the surface of the jacket. Do not use a penetrating coating.

If there is interest in 6m, a simple 3 element beam resembles a basic TV antenna and will work at heights of 12 feet or whatever the regs are on outdoor TV ant mounting. VHF 2m beams can be mounted on the same mast with a TV ant. A vertical may need more stealth work. A fold-over mast would be OK if the intent was to simply work it at night.

Then of course, moving. There should be a lot of cheap, foreclosed property (sad really) in the great state of Florida. They kicked it into overdrive with the foreclosures.