I traded in my basic Pearson 30 for an Islander Freeport 41 with generator, A/C, etc. Neither one is perfect for two. In the Pearson, we had to clean up dinner and put away the table before going to bed. In the morning the same thing the other way round to have breakfast. The bunk in the cabin is just a bit too small for two people. Storage in almost non existent. We ended up with a bunch of blue plastic totes in the quarter berth. It's no fun to pull out everything to get something out of the box in the back and then put it all back when you're done. If you're into camping that's fine but, for any length of time, not for us. Having to turn sideways to pass each other in the cabin gets old in a hurry. In fairness, the Pearson is more a weekender or big day sailer and there are other, smaller boats that are better thought out for cruising.
The Islander, on the other hand, is probably a bit too big. I can handle her myself, no problem, and the comfort is really nice but the PO wasn't real big on maintenance and I spend WAY too much time keeping things running. Almost every pump
or replacement. Half the stuff didn't work. When something stopped, the PO just stopped using it. In fairness, on a 30 year old boat, stuff happens but in this case maintenance was definitely deferred too long. Little by little, I'm getting things into shape and, I think, once I get everything shipshape things should calm down but I still think she's a bit too big for two. Don't forget that the cost of everything goes up by the cube of the length...dockage, hauling, everything.
For our lifestyle the best boat I have seen is the Islander Freeport 36 with the stateroom layout. Lots of room, a nice big bunk, comfortable cockpit, plenty of storage packaged in a hull that is a decent sailer. There are others with a similar layout. Unless you plan to make trans Pacific voyages where you need a snug sea berth for the times you're crashing through waves as big as an apartment building not the right boat, but I think most of us who cruise spend a lot more time hopping from port to port and at anchor
that in long offshore passages. What's right for you depends on your style, but I think waiting for "the perfect boat" is foolish. My Pearson "wasn't the right boat" but it was a boat and we put on lots of miles together. I sailed her for over 20 years before I traded up. I would paraphrase the cruising wisdom. Go as small as you can tolerate, go as simple as you can deal with, go as soon as possible. An extra year of cruising in misery is no joy.