I have sailed the Holder 14' among other smaller
sailboats and it is easy to sail and has a large comfortable cockpit for it's size. It will handle nicely in lighter winds but you may find yourself heading for (or staying on) shore when the wind picks up past 15 knots. I believe that the rigging for this boat is fairly simple too: 2 halyards, 2 sheets, centerboard pennant, rudder, 20' mast which one person should be able to hoist into place. I do not think this boat has stays on the mast which makes it even easier to rig prior to trailering. The Holder 14' is a fairly ideal boat for 2 people who want to do some casual sailing. Most repairs of this size boat can be done by you and thus will not cost a lot of money like they would on a larger boat with more systems.You have to determine if this is the right boat for the kind of sailing you want to do. I believe that I rented one and you should try to do this before you purchase your own. If all you want to do is enjoy some comfortable time on the water than this boat or the O'Day 17' would do nicely as they are both rigged in a minimal fashion. On the other hand, if you are a speed freak or an Alpha type personality and are competitive you might consider a boat like the Lightining 19' which are usually rigged for racing and are still being made (over 14,000 made). I bought one of these recently for a grand ($1K) with trailer and it came with 2 sets of sails and 2 spinnakers (which are not an option for most Holder 14's). The Lightning is a fast, sporty boat with a large cockpit that may seem a little cluttered compared to the Holder 14' as there are many more control lines (boom vang, mast rake, traveller, etc) you will need to become familiar with. My only complaint with the Lightning as a trailer sailor is that stepping and un-stepping the 30' (or so) mast is easiest with a crew of 4 whereas the Holder should be much easier to deal with in this regard.If you wanted to try sailing on a Lightning you might be able to get a position as crew on someone else's boat as there are several active Lightning racing fleets in Florida.