Re: Guide advice
If Tom is booked when you want to go another option is Derek Rust out of Marathon. My buddy from college used to fish with him when he guided out West and thus how I made the connection. Awesome dude and he really knows the water down there. We fished out of both Key West and around Marathon. He got me tons of shots at Permit which I usually fumbled.
Definitely make the trip. Saltwater fly fishing is a whole new world (and extremely addictive) but you'll have a blast.