Boat trailer dry will be right around 9000# so that gives you 1300# for stuff. If your full fuel and water, plus you gear you will most likely exceed the 10300 tow limit. You will get multiple answers and probably some on liability.
We had our 268 for 4 1/2 seasons and loved it. It was easy to trailer and get into and out of the water, plus roomy enough for my wife and I and 2 younger sons. Where it started to get small is when the kids were up in the 13-15 year range, then it was a little to small for comfort.
If you intend on slipping it, then bottom paint is an absolute must. We trailered ours for 4 seasons, and slipped it on the last one. Unless you want to pull and wash every 2 weeks, bottom paint is the only way to go.
As far as what year, buy as new a one as you can afford. 40K should get you something fairly new in this market. I had an 03 and never had any major issue, just typical maintenance and repair items.
Motor size, If I had it to do aver again, I would go with a big block, 8.1 I think. Especially if you have the genny, which i have seen factory installed on several used boats. The 5.7 with the duo prop is fine most of the time, but if you have any guests on, it was marginal IMHO. Ours didn't have AC/heat, but our new one does, what a difference, no question. I installed an aftermarket generator, and I wouldn't have a cruiser without one, for the type of boating we do.
You will like most of us have in the past outgrow it and get 2 footitis, or 3 footitis, or 4!

But it is a great boat and I'm sure you will love it.
ONce you find on vessel, be sure and have a survey done by a proffesional surveryor to flush out any issues prior to purchase.
_________________
Jeff
'14 Cruisers 380 Express "Simon Sez"
Merc 8.2 Mag MPI 380
DTS B3X, (x2) Axius Premier
(SOLD)
'08 V318
Merc 350 Mag MPI 300
DTS Seacore, B3 (x2)
