Speaking to the charter history question alone, we bought a boat that was in very
active sailing club use for three years. It was the model we wanted and with continued upgrades and repairs has become a fine and fast (!) cruiser for us for the last 15 years.
Do bear in mind that the old warnings about "rental" use of a boat adding about 5 years of wear/deterioration for each year of age are true.
The number varies, but you get the idea.
I did a multi-day delivery on a Ben 350 a few years ago and the layout inside was great, with a good galley and nav station. Of course that was their 80's design.
Best on luck on your purchase.