Sounds like you’ve gotten excellent, if not unanimous,
advice – already you can see a dividing line between those who enjoy the versatility of trailer-sailor, and those who are more comfortable with a bit more vessel under them. In the size boat you seem to require, the trailer-sailor will allow you to roam farther and wider, as well as maintaining the
trailer, brakes, electrics and of course providing a tangible justification for the
diesel F350-Dually you’ve secretly lusted after. My experience with trailerable boats convinces me that they aren’t for me as they sit unused and unloved – although many, many others have had exactly the opposite experience.
The
advice on the classic-plastic is much more attractive to me. I think TP pretty much nailed it, although I like the spin that Jim, Hamburk, Jeep and other introduced to rather round out the situation. If you plan to sail at least one day a week; then the boat will need to be in the
water (even if it is trailerable). It need not consume $50K or even half that with a little shopping… There is an
Ericson 35 (with apparently almost new diesel) near us offered
for sale at around $10K – what is attractive is the size of the
cockpit on some of these older club-racers… sure their age means you’ll pull some
maintenance (stay away from refurbishment, however…), but that is part of
ownership -- these like the aforementioned Catalina’s, C&Cs, 30-35’ boats are readily available, sail reasonably well for most of us and are generally quite affordable… not sure I’d be quite so draconian as TP, but many of these boats are in reasonable to very-good shape, yet modestly priced enough they won’t break the
family retirement account if they (shudder) evolve into a total lose…
At one stage in my sailing, some decades back, I was convinced to buy a larger boat than I really wanted (really wanted a Westsail 32, or 28) and learned a lesson – I don’t know who the
skipper was on that 15-ton
ketch we ended up with, but I can tell you who the maintenance officer was… for a “learning” boat, I’d stick to the 28-35 foot range (and that is a pretty large range), keep it simple and enjoy the heck out of it – you may just find that it is all you’ll ever want (as you add a trinket, gadget and/or techno-gizmo that we all seem to do…), or at least a boat you and your family enjoy for 10-15 years. If you set your
budget at $50K, you’ll find your “perfect” boat is right at $51K, so I’d entertain thoughts of a much lower
budget and just see what pops up…
To the extent it is worth anything, my advice is to buy a cabin that will just accommodate those you expect to sail with you, and buy the
hull and rig that you can handle all by yourself – because you probably will… Simple is good, real simple is really good…