Blue Water or Coastal Cruisers

[sailingdog]

Another reason I suggest the one-boat approach is that even if you don't lose money selling the first boat to buy the second on the boat itself, you will almost definitely have lost the money you spent on outfitting the boat. By buying a single boat that is well suited to handling both your short-term and long-term sailing plans, you won't risk losing money selling it to buy a second boat, and won't have to out fit it twice. The fact that you'll only have to learn one set of boat systems--engine, head, electronics, rigging--is a huge bonus.

[camaraderie]

The sounds of NC ad the ICW call for a shoal draft boat if you are going to be sailing rather than mmotoring in channels. You will need to get something with 5' or less draft or a centerboarder where the board can be raised to allow 5' draft. Your initial budget. Your budet eems to be under 100k from the boats you are looking at which is CHEAP for a 40' blue water boat...and any 40' blue water boat you find for under 100k will need a good deal of work to be ready for sea.
Much of what you want to do would be considered coastal/caribe cruising which does not require a blue water boat...only the portions heading north of Southern Cal. and across the Atlantic or Pacific would be within my definition of "needing" a blue water boat.
I agree with the notion of buying one boat suitable to your goals and learning on it.
So...I would suggest you consider:
1. Altering your budget to around $150k
2. Getting a smaller bluewater boat with shoal draft.
3. Altering your cruising plans a bit to allow for a coastal cruiser in the size you want.