Croc:
The boat winch that I bought at Harbor Freight for the lift, I re-cycled and is now on my trailer (I think it was around $25 bucks). Here is a pic of the winch on my trailer (look near the front, it's a pretty standard winch).
I started with a T bar hitch receiver that I bought at Amazon.com ( I think it was around $80 bucks), here is a pic of the T-bar receiver.
At the time we had 3 kayaks, one Oasis and two Revos, I tore a bunch of muscles in my back one day trying to lift the Oasis onto the roof of our Denali, (it hurt so much I pee'd my pants LOL). I was unable to lift anything for quite a while, so I bought the T-bar receiver to make it a little easier (previously I had four Malone stinger combo racks on the roof, two pointing forward and two pointing backwards so I would have four support points on each boat spread well apart. We would travel a lot around the country with our camper in tow, if I had to guess we had around 200k road miles with the kayaks on the roof. The Malone stingers were nice because they had a guide tongue that stuck out behind the car for loading.
Once injured, I could no longer lift for a while so I made a simple lift out of galvanized 1 1/2" pipe. Basically it was a 1ft and a 3ft piece joined together by a union. At the top of the 3 ft piece I put an elbow then another 3-4 ft piece of pipe. I mounted pulleys to the sides at the elbow, and at the end of the long horizontal pipe.
I would put the Tbar receiver into the hitch on the car, remove the top T part of the unit, and slide the 1 ft pipe into the top of the open end of the 3" square Tbar at the top (making a crane). I had the boat winch bolted to the side of the T-bar unit. To lift one of the boats I would pull the boat behind the car (sideways right behind the car). I had a 4 inch metal ring with lines tied to the front and rear metal lift padeyes, then at the other end I had stainless clips that clipped to the 4 inch ring. Everything was tied and preset at the balance point of the boat and I just left the ropes attached to each boat all the time, stuffing the ropes into the mesh pockets when not using them.
When I wanted to load a boat I would grab the ring clip it to the ropes, run the winch wire over the pulleys then lift the boat with the winch. Once up over the car I would rotate the winch around and set the boat onto the Malone wings, I would then remove the winch and push the boat forward to it's final position. I would then do the same on the other side with the other boat. Once the boats are loaded I broke the receiver unit down and stuffed it into the back of the car. The whole works ended up working ok and wasn't as heavy and bulky as it sounds. I started to worry about that 90 degree elbow joint maybe not being strong enough so I bolted a 1/4" x 1" x 1 ft piece of aluminum to the side at the corner at a 45 degree angle to re-enforce the 90 degree elbow. Actually on the long horizontal pipe I used two smaller pieces with a union in between so I could unscrew and break down the unit for storage in the back of the car, another reason is they only sell pre-threaded rod up to 2-3 ft lengths at the local hardware, if you needed a longer pipe you would need to thread it yourself (keeps the plumbers employed LOL).
Was it safe (probably not)
could you get hurt if it failed (probably)
did it work (yes, I used it for about 6 months every weekend until my back healed)
Once my back healed we ended up trading in the Oasis for a Tandem Island. The TI was much easier to load onto the Tbar than the Oasis ever was, didn't need the winch anymore so the winch system was retired.
Now if I'm not using the trailer, then I just load the TI onto the Tbar (just like the second picture above). It's actually very easy and fast, since you are only lifting half the weight of the boat at any time (about 45 lbs) it's actually much easier to load than the Oasis ever was because the boat is longer, and there are a lot better hand holds (I honestly can't tell the difference in the weights, the TI is at the most 10 lbs heavier it seems, but way easier to load).
What I do is walk the boat up to the car from behind so the rear is centered behind the car. I then walk the bow to the side of the car so the bow is even with the back wheels of the car. I then lift the front of the boat and place on my head, I then walk forward then sideways a little until I can rest the bow onto the tbar. I then center the boat on the T bar, then go to the back and lift the back of the boat and slide it forward. I actually roll the boat on pool noodles, it actually slides very easily. Then I just strap it down with the AMA's and sails stuffed along the sides. The boat is strapped to the roof rack in two places, then another strap at the T-bar (which is holding most of the weight). I don't do anything else on short trips, but on long trips like our monthly trips to our Key West place I also tie a safety line from the bow to the front bumper (we have no place to keep our trailer at the key West place so we just keep the boat on the roof all the time we are down there, (strapped down with HD motorcycle chain locks of course).
I'm not a big guy at all and my back was broken is a karate tourney when I was 45 (I'm now an inch shorter and my back has never been right since). Personally I find it way quicker and easier for me to just load the TI onto the roof by myself without any winch or anything, but that's just my preference. I'm out there every weekend, and when down in KW we typically go out every day (that means loading and unloading the boat daily), it works for us, that's all that matters, once you get a system down, it's actually pretty easy and painless.
Definitely get the sail set, we have the sails on all of our kayaks and never go out without them (kayak sailing is our favorite thing to do).
Bob
edit:
Oops I just looked at the top pick where I said the winch now resides, when I took that pic I hadn't installed the winch yet (sorry), the winch mounted on that alum brace in front of the bow (it's just a standard boat winch).