My number one criteria for choosing a surgeon was results: have they performed a significant number of surgeries, were those surgeries performed using the particular technique I wanted (peri vs. DI), and were those surgeries consistently good?
Sure, a local doctor may seem easier in the short run. Will you be happy with the results?
I had the option of going with a lesser-known surgeon 4 hours away (the closest "local" option) or going with a fairly well-known surgeon 8 hours away. I chose the latter, because of the number of surgeries he had performed and the consistently good results I had seen. If you're wondering, I went with Dr. Medalie of Cleveland, Ohio. That said, he wasn't the most well-known surgeon I could have gone to. I think Dr. Fischer in Maryland is somewhat better known for the procedure I had done (periareolar). However, I liked Dr. Medalie's peri results just as much as Dr. Fischer's, but he was closer and a bit cheaper.
Jay is right, this is a once in a lifetime procedure. If you're leaning towards Dr. Tholen, really, really look into the number of surgeries he has performed (since you mentioned Garramone, I'm guessing you're looking at a DI) and the consistency of his results. From what you've already posted about his results, I would proceed with caution. I suppose every surgeon has a period of 'practice,' of honing their skills. You say some of his more recent works look pretty good, but I would do the same as what you're already doing: look for more photos of recent work, since he didn't show all that many.
If given the choice of going with a local surgeon because of cost restraints and hoping it will be 'good enough' or waiting longer and going with a more established surgeon--I would wait. For scheduling, it sounds like you need to: 1) be sure that you can get accommodations in the time share, 2) make sure you can get time off of work for that time frame, 3) schedule surgery for that time frame. It seems like these are all things that are best scheduled months in advance. Is there any way that you can get a confirmed date for the time share, say, 6-12 months in advance? It may be further out than you were already planning, but it seems like the accommodations are the linch pin, and cutting things much shorter than 6 months may make it hard to schedule surgery (what's Garramone's waiting list like?). I don't know what your workplace is like, but I'm hoping that a 6-12 month notice of time off for something as important as a surgery date would be sufficient...
As for traveling after surgery: I did it. The 8-hour-turned-12-hour car ride (blizzard and black ice) was not pleasant. I survived and didn't hurt anything in transit (but do watch out for the shoulder strap on seat belts). However, I don't know what I would have done without my mother's help. I stayed in the area for 10 days, but when it came time to leave, I couldn't even lift my backpack of clothes + laptop without it hurting. Me driving wasn't happening; I was OK being a passenger--car or plane, it wouldn't have mattered. If you're doing this alone, you're going to have to pack very, very light, take a rolling suitcase, and not be shy about asking people to help you lift it up, if necessary.
One final thought: if you were to push the time frame you were planning on for surgery back, would you be able to save up more money so that cost would not be such an issue? Chiefly, would you be able to save enough so that you could get guaranteed accommodations at an extended stay hotel in Florida? That may make things simpler, especially if you can find a place very close to the surgeon. I'm not sure if driving yourself home after surgery is a great idea--you may have to take a taxi if you have no one to drive you. And for taxis... close is good.