[gulfcoastcruiser]

I have found trying to sail other people's boats greatly reduces my time on the water. I just like being on the water even if I am working on the boat at the slip though, so I don't get the same enjoyment out of using another person's boat.

I think I would go with option 1 and possibly consider up to a 30 footer. That is actually similar to my plan except I have more than 6 years to go.