To give your really useful responses we need to know what part of the bay you will home port in, and what areas you wish to sail regularly.
I have had a 3ft draft boat and now one close to 6ft. There is a difference. I can sail plenty with this deeper draft, but there were a lot of things I could do with the lesser that I don't do anymore.
Where will you be? What do you desire most of your sailing to be?
One thing about deep drafts is it can make passages much longer. You go way out and around a marker well off a point instead of coming across well inside. Enough of that and your 3 hr summer evening sail after
work becomes a
"go out to the entance of the channel and turn around to come back" instead of going somewhere interesting. A daysail to some location becomes a
"leave before dawn to get in right at sunset" (or later) because of the need to follow deep channels.
That depends on where you will be and what you want to do.
The Chessie has gobs of great places to poke into and explore. But if you have a 7ft draft there are a lot of places you just can't go. That can mean long passages down some coastline with no place to put in, vs having places because you have a shallower draft.
I'd have to really really really love a certain boat to get one with that draft in this bay. But I once swore I'd never have one with more than 4>4.5ft and now I am over that. But 7ft would be well beyond that...