Cruising Advice Needed!!! 2 or 3 cabin for 3 single guys?
This is not a question that strangers can answer. It is quite difficult for three people to live within the confines of the typical cruising boat. The number of cabins has little to do with that dynamic. Then there is the issue of who gets the ''good cabin'' which is either the one with the most comfortable motion, its own private head or the best ventilation.
There is also the matter of your choice of boats. You have mentioned some lighter duty boats. You will need to pick your weather windows and can expect a fair amount of maintenance costs.
While Captain Ron and I have a difference of opinion on this, I have seen a lot of boats that came out of the charter trade and spoken to a lot of people who have bought ex-charter boats. Except for Captain Ron,I have never seen or heard of one that I would classify as a good deal or in good condition. Even the ones that looked half way decent turned out to have their own collection of serious problems. If you go the ex-charter boat route make sure that you maintain a reserve account equal to about 20% of what you buy the boat for.
You need to understand that compared to private yachts, charter boats have an enormous amount of use, in harsher conditions ,and with people who are totally unfamiliar with proper operation of that vessel. While these boats do recieve basic maintenance, engine oil changes, sail replacement and the kinds of little year in and year out maintenance chores that are normal when you own a boat, are left untouched in the charter fleet. These chores not performed come back as frozen winches, blown up hardware, and dead engines, frayed running rigging, and so on.