This is not the place/board to mention the M word as there is much bias against it. For what it is worth they are very popular, very marketable, very versatile, very affordable, very resellable, etc. etc. You shouldn't be too quick to discount them over attitudes here. That said a class two hitch/vehicle is good up to 3500#. I also live and sail the PNW and find that securing a slip for the 4 months sailing season really pays off and provides many more sailing days in a season, something to consider.
As for 4WD on a pick-up, yes you will need it. I have seen pick-ups spinning their back wheels with an empty trailer let alone a loaded one. When the ramp gets cluttered from high tide & seaweed and then retreats half way down you may find yourself launching through all that mess and that is when things get slippery and 4WD is used. Been there, Seen it many times, I have 4WD and use it.