Looking for our dreamboat, we want our cake and eat it too

We’ve been talking about boat search without discussing our criteria. Let me back up.

How the boat will be used.
Well, this is going to be a liveaboard boat first, and a “one day I’m gonna” cruise boat second. So the boat needs to accommodate us as a family first and foremost.

As for the type of sailing, we’ll do weekend trips while we are docked at the marina. Eventually we will take off for coastal cruising (not sure when that will happen), but Tig doesn’t want to rule out ocean passages. So we want the impossible, we want it all!

Yes, we eventually came down to earth and prioritize our list of requirements. Below is what we have so far. This is just a draft. It will change over time and will be continually updated.

Sufficient storage space for living aboard as a family and configuration that will accommodate us (see this thread on sailnet about interior arrangement and kids). Some possibilities:

Two double berths

One V berth + 2 quarters

2 cabins (kids in V-berth, us in main cabin)

We are looking at boats in the 34 – 38′ range (down from the initial 38-42′). Tig is even dipping down and looking at some 32′ boats, but I’m not optimistic about them. Going small may help us get marine insurance (first-time buyers have more hurdles).

Fiberglass hull – no wood or steel

Must be in good enough condition to sail – we can’t be living on the hard for a year…

Less than 6 ft draft
Mast less than 55′ tall, for bridge clearance
Good quality construction
Rudder needs to protect prop shaft
Sails in good shape — it is a sailboat, after all
Can be single-handed

Nice to have
Cutaway keel or fin keel — ideally no centerboards or daggerboards.
Prefer a sloop or cutter (as opposed to ketch), keep it simple
Good engine access and systems access for DIY fixing

Icing on the cake
Composting toilet
Shower separated from rest of head (not a curtain)
Spinnaker sail for light winds
Less electronics on board
Good anchor — well, the anchoring system is important, but the actual anchor we can replace if necessary.

Some boats we’re researching
Contest 35 or 32
S2 11.0
Sabre 36/38
Wauquiez Pretorien 35
Wauquiez Hood 38
Contest 32
Sadler 34

Maybe a 1970s or 80s boat, an “oldie but goodie” may be a suitable vintage. Anything else we missed? Let us know if you see our dreamboat.