If I was going alone I would definitely seek a smaller boat, I spent quite a bit of time on a Moody 34 as a kid and that would make a great liveaboard for a single person or a couple I think. I'm going to be living with friends from my old uni's sailing club so the extra space might justify the extra cost, although as you say the tradeoff between space and safety is a vital one and it won't be a decision taken lightly. Serious ocean crossings won't be on the table initially too which will help, we'll mainly be sticking to our native Britain at first and then venturing into longer passages once we're confident in the boat. Obviously it'll depend on what's on the market when I'm ready to buy too, but I'm in no hurry and can wait for the right one to come along.