First, I envy you a little. With a 250K boat budget
you have a lot of choices, At worse, you might find your direction change after you get aboard. Long distant sailing is a bore to me. I have a great first mate but it turns out both she and I are much more party animals
with our friends than we knew. So we have changed our travel plans a bit and end up being home more that we thought we would. We were able to do it without changing boats. Of course, we had had 4 previous "live aboard" vessels. Luckily, we were able to sell all 3 for almost what we paid for them - so we had the fun, used them and was able to recover a lot of our expense. Of course, all 3 were used boats when I bough them. But I also did not have your budget
to work with. (Ex's got that) If you really enjoy your boats, you will not regret. Of course, there are people who do a lot more looking back than I do. I am pretty good at looking ahead.