I had a 35 footer in charter. It was a good tax off-set, and as many of us don't, or are not able to use a boat all that much, it is a good way to defray costs. Especially if you have it under a professional hire company, who then look after all maintenance, supplies, linen changes, and hire crew training etc. For a percentage of course.
However, there are some issues. One important one is not being so able to personalise it - and keep personal stuff on it. However, the expected concern of it being mistreated by rank amateurs was not actually the case. Rental crews tended to be very cautious, and respectful of it in our experience. The main issue from a practical point of view is limited opprtunity to work on it, and perhaps most importantly, depending on where you are and your local laws, is how nit-picky they are regarding survey requirements. Here in Oz, the laws are pretty tight, so unless the boat is built to survey, as ours was, it is often not possible to get the vessel compliant later in a used boat, as it would be just too expensive.
On the other hand, being able to book it in advance, and have it all stocked, cleaned, fuelled and ready to go - and just being able to walk off at the end, did have it's attractions. That and the tax off-set.