So, how big is yours? Why did you choose that size? Does size matter...?
Size most definitely does matter. Others have covered most of the considerations as you go up in size: comfort, convenience, draft, purchase cost (new or used), dockage, maintenance effort, lines, sails, fittings, hardware - it all goes up exponentially with size (except dockage which is linear). Ours is 50' on deck (when you're paying by the foot), 65' sparred length (when you're bragging in the bar...). Is is comfortable: absolutely! Headroom? Check - 6'6" to 7'+. Is it impressive? Absolutely. Is it great for cruising the islands? Yes and no. It needs a fresh breeze to really sail well, and it does point to wind well. Once you get there and anchor, it is a great platform. We bought her with the intention of cruising, and that is what we are doing. But, it draws 7'+, so that limits some of the anchorages and some of the places you can go. Need a dock - think end "T". Need a haulout - plan ahead, as who can haul out 39 tonnes are limited. If we had it to do again, would we - probably not. Do we want to sell her - no way. We fell in love with her when we saw her, and especially the charm of the craftsmanship down below. That's the kicker - boat buying can become an emotional decision rather than a rational one. Try to avoid that when setting your expectations. I'd say, once you have decided rationally what you are going to buy, only then let your emotions influence which of the options that fit your criteria you actually select.
I know what a handful a 42' boat can be, and it is pretty much the limit for single-handing because when you need a sailing day, who want's to go looking for crew?
Couldn't agree more. I think 42' is a good number on the upper end. We get seduced by the spaciousness and looks of the bigger boats, but bigger is not necessarily better. As others have posted, it really depends on your plans, and of course, your desire or propensity for frills.
Above all else, I would place how well it sails at the top of the list. If you intend to sail, and not just motor your sailboat, you want a boat that will SAIL. And to Gunni's point, besides the question of crew availability, even if you aren't singlehanding, it is nice to not have to have the entire crew engaged in the actual process of sailing, unless you are racing.
I have one thing further to add with respect to those who buy new boats. Good for them, if they can afford the new boats. Without new boats being bought, builders can't sell new boats, and if they don't sell new boats, they can't keep making them. We need a source of used boats feeding the market. After all, all used boats started life as a new boat - and someone had to buy that new boat to get the process started.