I thought I might elaborate a bit more on the subject of draft, which I mentioned earlier. I recognize now that what I previously wrote was somewhat ambiguous:
Your homeport will be in relatively shallow cruising grounds, so you have a hard requirement for moderate/shallow draft. The boat that is ideal for your immediate purposes of coastal sailing with shallow draft, may not end up being the ideal boat for jaunts out to Bermuda (especially as you move up into the larger size range.)
What I meant, very generally speaking, was that as the boats you look at get longer/larger, the negative affect on performance of the shallow draft constraint will increase.
Using extreme examples, on a 20 foot boat, shallow draft might mean 2-3' draft. On a 50 foot boat, it might mean 7' draft. But if you were to give that 20' sailboat a 5' draft, it would be considered "deep draft". The 50' sailboat with the same 5' draft would be considered fairly drastic shoal draft.
The 20' boat with the 5' draft would probably perform extremely well to windward. The 50' boat with the 5' draft would likely be very compromised to windward.
The example above is a bit of an oversimplification, as there are other factors involving hull form and keel span, but I think it's useful for illustrative purposes. I guess the message, in other words, is that "shallow draft" is a relative term.
This is something to keep in mind as you search for your new boat. Your requirement for relatively shallow draft means that you should look not just for a boat which fits the draft requirement, but whose performance also is not unduly hampered by it.
The good news is, your requirement for sub-5' draft should not be too difficult to meet. And as long as you keep the boat size modest, you should be able to find a decent performer as well.