A Philoshopical Question
This is very late, but comes from someone who knows about sitting on the fence and delaying decisions:
As I read your philosophical question, it seems to me that the real problem is that you are keeping yourself from making a committment to act because of the <em>possibility</em> that you <em>might</em> want to go offshore. You fear that if you make a decision you will lose a set of possibilities. But not committing leaves you in a state of limbo (and there ain''t no boats in limbo).
I agree with Jeff H: commit to the idea of coastal cruising, which you acknowledge will keep you busy and happy for a good long while, but hedge your bet a bit by choosing a boat that has some offshore capability. Combined with your un-hurried sailing style, you then can sneak in a bit of blue water and taste that experience as well.
It will feel good to have decided. Then the plan you have committed to will be able to crystalize in your imagination. More importantly, you will finally be able to <em>move</em> toward your goal, since you finally have a tangible one.
Why miss out on so much "good" because you''re waiting, hoping for a slim chance of "great"?