live in Key West
 

I have never flown for the airlines so forgive the ignorance. Could someone fly for any regional and live in Key West or would life be too hard at some and better at others commute wise?

Nonstop flights and lots of them make commutes easy.

Connections to an airport served infrequently that commonly has weight restrictions, such as Key West, make commutes hard.

Depends on how much pain you want to put up with and where you end up based.

Something with a Miami base looks do-able. Atlanta would probably be ok. Anything else would be painful. And remember that bases change frequently, so what you have now might not be what you have in 6 months.

Commutes pretty much suck no matter where you live but some are worse than others. Eagle has a MIA base but I'd never recommend anyone apply there. Seaborne is seeing some growth but I don't know what their bases are. I'm not too sure who has bases in the south east, I'm a west coast guy so I only looked at west coast bases.

Silver has a Ft. Lauderdale and Tampa base, but unlikely to get either of those. They need pilots, so it might be worth a shot.

Lived on a sailboat in Key West for two years. (2006-2008) Had non-rev privileges but found few empty seats available. There were some airline pilots living on boats in the Keys and they found non-rev / jump seat difficult.
Most just drove to Miami.

Lol recommend someone to go to Seabourne vs Eagle. Laughable.

Their upgrade time is short if I'm not mistaken. I has a friend there who did it ~2 years. Eagle is still 7+ and holding strong.

There are a number of pilots and flight attendants jumpseating from MIA to EYW. It's not always easy but Eagle has quite a bit of daily flights so if you plan properly you should be able to make it to MIA at least. I've seen DAL 737 and SWA 737 fly their daily as well. I believe they fly from ATL and SWA from MCO.

No matter how you look at it, if you have to do a 2 leg commute to get to work it's very tough and tiring and you will probably get burnt out. If you can fly for someone with a base in ATL or better yet MIA, life would be much easier if you plan to stay in Key West.

P.S. Don't listen to anything Bzzt might have to say about Eagle, if that is somewhere you're considering applying to.

St. Croix and San Juan for Seaborne

Sure, their Pilots and FA have problems getting paid. Second, you have to sign a 2 year contract.

You can upgrade but will make less than 50k as a captain. Based in St Croix or San Juan, commuting from key west have to be double leg and MIA to SJU are always full!

Upgrade is not everything in life.