Hey Spawn Sack
I'm a big advocate for the truck and camper route. Great for accessing those out of reach spots, everything all with you when you need it. Plus great for long hauls when you're pulling into parking lots etc and you don't need to take up 6 parking stalls.
I bought a ford ranger 7 years ago and an import camper to go with it. It's an Adventurer 76R (which has now been discontinued.) It's a great little rig, double bed up top table folds down to another double, sink, stove, heater and 2 way fridge. That unit had gone a lot of places including up and down the coast to California at least once a year. The bonus with this type of set-up is you have a smaller truck when the camper is off for commuting.
Most of these import size campers don't have a bathroom, which wasn't an issue for us, but may be to some. It also reduces the weight by not having the tanks. They do usually have a generous fresh water tank but do check on that as if you'll be off the beaten path for awhile it is something to consider. The pop-ups are nice for the clearance but can get colder and do have a bigger risk of leaks. As well, like tent trailers, they need to be aired out properly as if it's wet when it gets packed up they're can be an issue with mould building up. We went with a full hard sized unit and use it year round.
A couple things to look for in a camper. Go with a full one piece roof, this is where most of the leaks occur so get a one-piece roof. If buying used, check the seals and caulking around the vents and windows make sure they have been kept up. Check the height of the cab-over as you may need to add some wood or something to the truck bed to raise it up properly.
As for boats on the roof you can get roof racks and pitch a small canoe up top. I often load kayaks and surfboards on ours so it's not a big issue. However with something a bit bigger or for convenience I might suggest getting a boat loader. Something like this.
http://www.loadit.com/rear-boat-loader.htmlAll in all they are a great way to camp and I love ours. I recently upgraded to a bigger truck and now I am torn on our little camper. The wife wants to sell it and get something bigger but I love our little camper. Plus they are getting harder to find and everyone i know that's owned one and sold it has regretted it later.
Hopefully that's of some help.