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.
RANGER 20
SAN JUAN 21
SANTANA 20
CAL 21
Medium car (I think this is what the OP has):
Cal 20 , sleeps 4, pretty good performance, well enough built to go
offshore with some mods, $1-3k.
RANGER 22
RANGER 23
SANTANA 21
CAL 22
COLUMBIA 22
Larger vehicle:
Catalina 22 , sleeps 5, good performance, would take to Catalina Isl. but not
offshore, dinette.
SANTANA 22
Bigger
budget but still medium car:
J22, high performance, sleeps 2-4, $6-10k.
Large vehicle and budget:
Hobie 33 , excellent performance, sleeps 5-6, low
headroom but not really camping so much, $10-20k.
Montgomery 23, 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.