You are correct in saying that you do not buy a boat for resale value. However, it can be one of the considerations in making the purchase.
A little background may be in order here.
The Major (Can't call her the Admiral 'cause she's in the Army) was called up to active duty for a 2 to 3 year stint. She is in Sacramento and I'm up here in Oregon. I did take a horse down to her to keep her out of the bars. I travel down there about once a month for a long weekend and she gets up here about twice a year. Our main combined hobby/pastime is our horses. She rides and I ride and train them.

Latest addition this spring --Misty's Moon Twist
Sailing is a hobby that we are just getting started on in the hopes of pursuing it with more gusto at retirement (5 years). Since she is not around up here, my thought was to get a little bit bigger boat than the Holder 14.
The Mac 19 seems to be a resonable priced interim that would be easy to single hand and not lose too much additional value when it comes time to move up.
http://cgi.ebay.com/ebaymotors/ws/eBayI ... AMEWA%3AIT
I'm not thinking of it as an investment, but the Scotish in me hates to throw money away. The 19 would be used as a day sailor only, and would let me get more experience till the Major gets home. Also, being a true power sailor, it is more suited to sailing on the Columbia River, which is only about a mile wide around here. Makes beating up wind a pain to get home before dark.