So we are now looking for Womboat 3 and here I think we need to be damn careful. Our sights are set on 40' and we are very much trying to keep that as a maximum size knowing just how expensive the gear becomes for every extra foot. In fact, not just the cost of the gear but also the handling thereof noting as well that the bigger the boat the more difficult she is to berth, or indeed to find a berth. (by that I mean temporary berth in ports away from home.)
That was a concern for us, as well. Frankly, I could afford a bigger boat and was lusting in particular after a Kanter Atlantic 45...very much my kind of proposition. But my wife is a wiry five-footer, and while young and game and pretty strong for her size, simple physics means I have a pretty good idea of what she can and can't overcome in the boat handling department (luckily, she's fearless about jumping off with a spring line in her teeth!). She can manage sails on our 40 footer in 25 knots entirely alone, which means for the duration of her watch. It is unreasonable to expect that I can be "on call" weeks at a time on passage, so it was her physical limitations that determined that maximum boat size we could handle, as neither of us wanted to get into electric winches, etc.
Of course a 40 foot full keeler has a LOT of stowage, tankage and general hidey-holes, so that's not an issue, and the pilothouse gives a vast amount of privacy for the aft cabin plus great engine bay access. We've lost some excitement in the sailing realm, yes, but have stability and durability on the upside...you just keep on plodding on at five knots in all but extreme conditions, because the boat drives itself, largely. Also, if the hydraulics fail, I can steer via tiller, but 40 feet is as big as I'd want to do that trick.
The price factor comes in later, but I do admit that ground tackle is massive enough at the 40 foot level (particularly if you size it up one class) to discourage wanting to go larger. More space means more crap aboard and sometimes it's best just to let the boat's dimension dictate what truly needs to go sailing with you and what can be left ashore.