of thumb has always been to buy the smallest boat you can be comfortable on for at least a week for anything that you are talking about 25+
I love the Yankee's. They were great boats and after they went out of business, pretty much saved Catalina
and gave them something other than the great Butler Designs. Robert Finch did the 24-28 and the 30 and 38 were SS designs. Cape Dory's are great boats as well, we currently own one. Remember the draft
for where you are planning on sailing.
From what I heard you say, you may want to look into a Compac or Seaward
25. These are both trailerable and setup for thin water
sailing. The Seaward
25 holds it's value well, but plan on spending ~ 15-25K for a good one on a trailer and be careful with boats made prior to 1995. It is a good boat to get the wife into sailing as there is a full head
and fairly decent galley
. If you are 6' tall or over, you will not be happy with a trailer sailor. Catalina 25's are good choices as well. I like having a diesel
and the ability to put a high amp alternator
and extend the cruising if I choose, so that was a big factor for us when I got my current
wife into sailing.
If you have USAA, then age is less of a factor for loans, but the other banks require the boat be 25 years or less and loan on nada (which is far below market). You will find that if you are financing
that you are limited and not able to get as good of a deal. Boat values are really based on the ability to finance where you see them really drop in value once that magic 25 years sets in and the next owner must pay cash, or a substantial down payment. Again, USAA can't be beat if you qualify for membership
Beam is important if you want a trailer sailor or even a boat that can be cheaply moved out of the water. 8' 6" is the magic number for not requiring a permit
to move in most states.
I brought up the idea of getting my current
wife into sailing. We stated with a Seaward 25 and she enjoyed it enough to move up from there, so it was a wise choice that cost a little more up front, but held it's value and made a good stepping stone to get her excited about moving up and sailing to further destinations.