Wes,
You have a lot of open area to cover there.
You say trailerable, and I assume you mean that to be trailer launch
capable (there are many small boats that are on trailers that do not
launch and recover very well at all).

Start at:
http://www.trailersailors.com/index2.tpl

These are the people that are doing what you want to do. They have
lists of boats (links to type-sites) and stories to read that will all
help you in your search.

Then find a local small boat marina or club and try to locate the boats
you are interested in and ask the owners about the experiences they have
had. Have your seabag with you as this may well result in an invitation
to go sailing.

The boat I have now is a big trailerable. It is so for lots of reasons
and I am glad for it.

I have learned -
"Where there are boats with masts, there is either someone I know or
someone I should meet."

Matt Colie A.Sloop "Bonne Ide'e" S2-7.9 #1
Lifelong Waterman, Licensed Mariner and Pathological Sailor

Wesnkat wrote:
I know this is probably a often asked question, but here goes (maybe again).

I have a great Hobie 16 that I have sailed in Mission Bay, San Diego for the
last 8 years.

But now, I've got a lovely wife and two kids (6 and 2). Bottom line, I need
to ditch the cat and buy a monohull that is fairly dry and cozy for the
family members.

I am looking for a used boat that is:
1. trailerable (i.e. light and swing keel; I have a Jeep Liberty to tow)
2. inexpensive (under $4000)
3. easy to sail by one or two people
4. extremely safe
5. fairly fast under sail (I coming off a cat after all)
6. able to handle an outboard motor
7. has a cabin.

Been looking at MacGregor (19?) and Hunter (water ballast systems seems very
safe), and Catalina.

Any advice on these or others would be greatly appreciated as well as where
to look to buy.

Thanks,

Wes