If you truly can telecommute and work anywhere, Key Largo has several shops that have well regarded instructor programs. Key Largo also has some of the best diving in the USA.
If you need to be near big companies or healthcare firms for your IT work, then Dade County, Jacksonville and Tampa are your best bets. But all are big cities with normal big city issues like crappy traffic. However, they have more high paying jobs than most other places in Florida. Miami-Dade would give you a springboard to dive in the Keys, dive in Miami or anywhere between Jupiter and Miami. Jacksonville is known for spearfishing rather than sight-seeing diving, but I've never dove there.
For quality of life and good diving, its hard to beat Palm Beach county if you have a family. There's little traffic on the north end of the county and the diving is great. Even on the south side of the county, traffic really isn't all that bad compared to places like Chicago, LA, Miami or other big cities. The pace of life is slower than big cities, which may not be great if your single but I'm fine with it! However, high paying jobs and large companies are less abundant than the big cities.
Broward County (between Miami-Dade and Palm Beach) has some great shore diving and provides easy access to Keys or Palm Beach county diving.