Some thoughts:

I think your personal preferencse for accomodation may indicate the size
boat you want. Almost any sound well handled vessel can work those
waters. In grade school I sailed there in a 12 cat boat and fished in a
16' outboard. It gets bouncy and exciting if you don't pay attention to
the weather, but that's true regardless.

Do you want a dry warm steering position, or just fully protected from
spray, or will a little spindrift be OK sometimes? Sun protection? Want
to be able to fully enclose the cockpit with isenglass for rainy days at
anchor? BBQ? How much of a head do you want? Basin? Shower? On board
water tanks or just some jugs? How much storage? Large comfy bed for
overnighters? Icebox or just a cooler? Multiburner stove or just a
gimbaled burner? How many in-laws and such do you want to carry at once?

And, as mentioned above, do you want to mount radar (plan on spending a
bit of time learning how to make it work and how to read it)? If you
plan to ever anchor, you'll want a useable foredeck, not one of those
sloping skidplates lately popular.

A larger boat that you enjoy staying on may pay back some added costs in
saved hotel fees as well as providing more dignified travel.

Rufus