I can't say what is right for you, but you're not signing up for life, are you? You could try one for a year, then the other, then decide. For the first year I owned my larger boat I was visiting all the time for work and projects. I was constantly out there in the evenings removing and installing stuff -- sometimes the same things, if I screwed up! I'm 30 minute drive to the boat, so it was not much of a pain, unless if I forgot a tool at home. After a few years, you work on improvements less, so you don't visit as often for projects, only maintenance and sailing. Perhaps you should try the closer place for the first year, and see if you mind the motoring, then try Option 2 after you finish all your initial projects?