I weighed a very similar decision 3-4 years ago and we ended up
buying new as our first 'full-size' (

) boat - which is arriving imminently for this coming sailing season. It was a close thing, but we looked at the following:
* Warranty coverage, however difficult, at least gives us a starting point for
repairs and replacement for items that don't
work. By the time the warranties run out, we're hoping that we know better what we're looking for in
replacements or
repairs.
* Concerns about previous
maintenance. We're under no illusion that this boat will arrive perfect, but we will be able to maintain our own records from 'minute one' of how everything was maintained and not have to worry about guessing or hoping for the best on potential hidden damage or issues. We've had to spend thousands of dollars in our house on what was 'unknown' but definitely known damage when we bought it.
* Fractional program: While we
work over the next few years, we're putting the boat in a fractional program. This will defray some of those costs (while admittedly running up the maintenance), but the local manager is super committed to working with me on boat
maintenance and education for the future upkeep.
The biggest suggestion I have, if you buy new, is to really engage with your
broker and make sure you have a good rapport there. We're at the bitter end of the
purchase process, and looking back would definitely have asked the silly questions and belabored the silly points to avoid some of the confusion at this stage.