Thanks for all the responses they are greatly appreciated. It sounds like almost everyone says to avoid chartering if possible which seems reasonable. Might be better to go smaller/older on the boat to keep the price down. Then I can just keep it on the hard the rest of the time. The place I did my sailing courses (San Diego Sailing Academy) might be the one place I would trust a boat to charter. Those guys kept those boats looking awesome and took care of the little things that invariably pop up on a boat. However you are still at the mercy of the charterers in the end.
I'm thinking I need to get hard numbers on the associated costs of insurance, dry storage, etc for various locations and then see what makes the most sense. If I'm not going to charter the boat then I could check into keeping the boat in the Caribbean somewhere and then just fly in/fly out. I met a cool group on my last trip to the BVI that were doing a circumnavigation in stages that way. They would cruise and do a leg then leave the boat on the hard until they had more time. That was at Virgin Gorda Yacht Harbour so I'll check into some arrangements like that. However, I also loved sailing in Florida when we picked up our Seaward a couple years ago so that would be an awesome option and probably half the cost.
As to johnnyquest37 question about could I move somewhere closer to the water, that is definitely something that I have seriously considered. I actually just turned down a coastal position for numerous reasons. The thing about my current position is I could take more time off for the same amount of $$$. Unfortunately physicians get paid less in prime coastal areas. Not to mention my cost of living in Kansas is super cheap in comparison to California, Washington, Florida, and some other places I've checked out. This plan seems to make the most sense to me. As far as boat projects and the "putter" factor I still will have my 26rk to mess around on when I'm back in the mud puddle.
Thanks again for all the responses and keep them coming. Be brutally honest too if there is something really stupid about this idea also. I have thick skin