Is it just you, you and SO or 2 of you pluss occasional guests or do you expect to have guests overnight regularly?
-What level of comfort are you expecting?
-Berths and toillette below is obvious.
-Do you require a table to eat at below or are you happy to sit on you berths or in the cockpit
-Does the head
need to be enclosed?
-Is sitting headroom
adaquate or do you require more?
These questions will have an impact on the choice of boats that might be appropriate.
Assuming a willingness to 'camp' and small car to tow with:
Holder 20 , sleeps 2-4, great performance, $2500ish.
Wylie Wabbit 24, sleeps 2-4, excellent performance, $4kish.
SAN JUAN 21
Medium car (I think this is what the OP has):
, sleeps 4, pretty good performance, well enough built to go offshore
with some mods, $1-3k.
22 , sleeps 5, good performance, would take to Catalina Isl. but not offshore
but still medium car:
, high performance, sleeps 2-4, $6-10k.
Large vehicle and budget:
, excellent performance, sleeps 5-6, low headroom
but not really camping so much, $10-20k.
, Cruiser, potentially offshore, sleeps 3-4.
For someone with limited experience I would go with the Holder 20, light, cheap
, easy to rig and derig so you can go daysailing on any lakes that might be in the area. But still big enough to overnight on.
In a couple years you will have a better idea of what in a sailboat makes your heart go pitter-patter and you can move up.