Ive been around the charter industry since the early 90s as a client, boat owner (2), charter
captain, sailing instructor, etc. Ive been very involved in the operations of several charter companies.
There are also many threads here discussing the subject of putting
boats in charter...good to take a look at those too.
Bottom line: if you are looking to actually make
money, whether cash-on-cash income, or long term apprecaition...a boat is not the way to do it.
A typical outcome is that charter revenue can cover a lot of the cost of
ownership, but there is always yet another unexpected expense to chew up any meager returns you make...especially on an older boat. In the end most break even more or less.
The charter companies that will be interested in an older boat are few and far between. They are mostly small mom & pop shops. That can be fun if its run as a club like
environment, but often their
maintenance procedures are not the best (though there are exceptions).
Also, trying to part-time
live aboard a charter boat is going to be problematic for several reasons. Suff & systems: A charter boat should have nothing aboard it that does not relate to its charter
service and its systems should be as basic as possible. So, personal items and additional creature comfort systems are not ideal on a charter boat. Revenue: the more an owner uses a boat the less revenue it produces...not good for the charter company or the owner. You may find a mom & pop whose charter traffic is primarily on the weekends which would make part time use during the week easier. Maintenance: if you do find a mostly weekend traffic charter co...guess when they will need to do maintenance.
If what you ultimately want is inexpensive part time lodging, then that might be feasible if you can find the right charter co fit. I used to have a boat with a mom & pop that I used frequently.