Don't forget - not all charter companies are equal. What hallucination says is accurate for many companies, but not for Moorings/Sunsail (and perhaps others) as you pay nothing during the charter contract. They take care of all maintenance..etc. The only downside to this is that you can't customize your boat - you can choose from the models they offer, but they all have the same features.

Personally, I don't see that as a big drawback since the more extras you have, the more things people can break, so you can just add the extras once it comes out of charter as the majority aren't needed when chartering.

The other thing to consider is having your boat be a crewed boat - these get taken care of much better.