Our boat is really our summer home and we sail her nearly every weekend for 6 months per year. Having enough room and amenities to be comfortable is important to us. We also have guests nearly every weekend and they're not always family or close enough friends that we would be comfortable camping on top of each other.
Our boat absolutely sails like a dream. Easily handled by 2 and, while I've never taken her off he dock alone, I have effectively sailed her solo with my wife down below many times. Essentially everything is in the cockpit.
Certainly, the larger boats get your attention with every maintenance bill. I fully agree with the comment above that we are always met with a huge smile from maintenance yards. They are absolutely accustom to seeing dollar signs, when they see a bigger boat. Our bills are going to be bigger than a smaller boat, but they can really reach for it, just to see if you'll pay. Let's face it, there are some uber-rich owners that just want it perfect at any moment and do pay for that kind of attention. I manage my own maintenance, doing what I can and contracting out what I can't or don't have time for.
The one thing my wife often complains about is the size of the fenders and dealing with them. We use 12" x 36" fenders. Six of them. You would too, if you've ever had a bad storm destroy a 30k paint job. From time to time, I think about buying inflatable mega-fend fenders just to stop the complaining, but that would be $3,000 in fenders!!
We sometimes dream of moving up, but certainly don't need to. Who knows, maybe in retirement, if things go really, really well between now and then. But the idea of less expensive, easier, etc, can't escape one's thinking either. If it were just the two of us, no guests, we could certainly be comfortable in something smaller.
Then we rented a 36 foot Bavaria for just the two of us in the BVI last winter. Fenders the size of my wrist!
While there was plenty of room for two people, it drove us nuts. Boat speed, galley storage, having to climb around the helm wheel or having to remove it at each anchorage, and on and on. I absolutely could not wait to get back to the helm of our boat!! It was great therapy.
The reason we know we have the right boat for us, is we are always comparing every other boat we are on to it. We've toured similar sized Oysters, Hylas, etc and, while acknowledging their quality, still prefer many of the features of ours over them.