The DS is a very versatile boat. It can be sailed very easily and conservatively with little heeling (don't forget to put the centerboard down - don't ask how I know this...) and is great for a beginner.
BUT it can also be a wild ride, main sheet pulled way in with a flat sail on centerline, hiking way out with the tiller extension in your hand, feet under the hiking straps, and the spray in your face.
Check out these pictures (which I can't seem to make appear in the post, despite using BBCode...)
http://album.sailboatowners.com/detail?photo=3145
http://album.sailboatowners.com/detail?photo=4187
It'll be more like a surfboard than a J/24.
Once you get the hang of things you ought to be able to rig it up in 30 minutes easily. I flake or roll the mainsail on the boom, ready to haul up as soon as the boom goes on, for instance.
If you want ease of rigging, find a boat that has a mast step hinge. (Some of the Daysailers have a keel-stepped mast, which means you pick the mast up vertically and drop it into the hole in the deck and align it with a pin in the bottom of the boat.) With a hinge it's easy. Unstrap the mast from the mast crutchs, move it aftward until the hinge lines up with the mast base, pin the hinge pin, then walk it up into vertical position. With this boat you can set the shrouds to the correct length, leave the mast down, then when it's raised the shrouds are already adjusted - nothing to do. You MIGHT have to slacken the forestay to pin that, but usually just pulling taut on the halyard pulls it fore enough.
It's really thus raising the mast, pinning the forestay, bending the sails on, throwing the motor and rudder on, attaching docklines and fenders, and getting it in the water. Oh, and don't forget the sunscreen.
carlos