One thing I would encourage you to reign in is your trepidation about operating a larger boat. It is something that most people get past very quickly. For me it was a much bigger adjustment from my 26' cruiser to my V358 than when I moved up from my 21 footer to the 260. But I spent time with a captain and lots of time around the docks before they filled up for the season. By the end of the first season I was completely comfortable. I know I'll be moving into an even bigger boat at some point and, while I know there will be a learning curve, I have no anxiety about making the move based on the inevitable adjustment to to handling the boat (the bigger boats get, in most cases, the easier they are to handle).
While it seems like you're keeping a careful eye to budget, as the cliche goes, buy the biggest boat you can afford that fits your needs. Everybody's experience, budget and needs will vary greatly, but my 260 - which seemed so huge the first few weeks I had it - got very small very quickly
based on how I was starting to use it. Storage space, a premium on any boat, was a particular challenge on the 260 if I had just a couple of people traveling with me. Our overnight bags always sat out in the cockpit overnight. If you can make the numbers work on a slightly older but bigger boat and it will still serve your needs, I'd encourage you to at least look into it (and again, not let the perceived difficulty of operation hold you back).
I bought my 260 thinking I would still pull skiers. I did once. But that was never a big part of boating for me so it was easy to let go.
Having said all that, it is a great move to be making and you will enjoy all of the self-sufficiency that comes along with having a cruiser more than you can imagine. It will open up a world of possibilities with how you boat. I would also add that coming from a cuddy it may be less of an adjustment than were you coming from a bowrider or deck boat. Are there days I miss the ease of untying and shoving off without dealing with shore power, water hoses etc.? Sure. Would I trade that for the new adventures being in a cruiser have brought me (including the incredible eight day journey I once took in my 260)? Not for a second.
Good luck with the hunt and let us know how we can help
