My first sailboat was a West White Potter 15, and the rig couldn't be simpler. I could raise it by hand without any mechanical assist, and it was a simple 3-point rig secured by pins. It still took me about 20 minutes to setup or take down and secure all the parts... 20-minutes of a LOT or up and down climbing and bending activity. I was in my late 20's in good shape, but on a hot-humid day it took its toll on me and I decided my next boat would be kept in the water ready to sail, full-time. Even then, it involves some work to cover sails/uncover, close/open thru-hulls etc. every time you sail.

It's a lot of work to rig and de-rig most sailboats. Even small ones take a half hour or more of laborious effort, and anything with cruiser capability would take hours and possibly require a crane or leveraging high loads on winches and blocks (potentially dangerous if you forget a step or have equipment failure). If you're going to trailer (and can't leave the boat rigged right next to the water) a power boat makes more sense, IMHO, unless it's only going to be used a few times a year for vacations or seasonal storage.