But I don't think I'd like long-term cruising. My wife feels the same way. We love vacation sailing and could even see going for a year or two, but we both have pursuits and relationships we enjoy that keep us tied to this area. We've both got business that would be hard to restart. Even if we went for a year we'd still commuter-cruise to keep the plates spinning. We don't feel like we need to be "liberated" from anything, we like our "stuff" or "junk" and worked to get it. We love vacation cruising for a lot of reasons, but once the novelty wears off; "what day is it?" can get boring, and taking a whole day to get ice and do laundry is not real challenging or exciting.
Quite frankly I think it would be boring to live on the hook, unless we made lots of excursions/trips at various ports to get to know the people and places we'd visit. The trek down the ICW sounds like not a lot of fun. There might be some nice stops and scenery but I view long days of motoring as slow torture.