The truck bed camper is a great compromise and it gives you the most flexibility with the least investment. I too looked at those but was shocked at how much they weigh! Choose your pickup wisely!

I think in David's case, where he already has an SUV that can handle the camper, the camper mod might be the way to go but the modifications could be pretty involved. Storing the mast (and sails) could be a little troublesome but would just take some forethought. Upgrading the axle, springs, and tires (if necessary) would probably be about $250 and an afternoon. Extending the tongue is a bit more involved but certainly possible.