Per buying your own boat, vs getting a ride, there may be other factors. In my case, the lake were I sail rarely has any other sailboats on it, on the Sunday afternoons when I sail. That means if you were in my situation, you would be hard pressed to get a ride. So ask around first. Second depends mostly on you. I have a coworker who wanted to buy a boat and learn to sail. He had only been sailing on one other boat and that was some time ago. I told him he really needed to go for a ride first, and get over the biggest humps with help. With him, one ride got him most of the way there. But that was because he was an aeronautics engineer, so he knew more about foils than probably anyone on this forum. But for the most part, he had good mechanical aptitude, so everything he could see made sense. Some just easily pick up on things.
The second question seem to be about launching. That has me scratching my head. Unless you are launching into current, a strong wind, I don't know what would be difficult about it. If you launch by yourself, you may want to bolt on goal posts on your trailer, so the boat doesn't wander off before you have a chance to get out of your car and tie it off. Even so, I have done it, where I partially launched it. Tied the back of the boat off loose, and then put it in the rest of the way to get it off the trailer. the rear line prevented to rear of the boat from wondering off. One other trick I do is have an extra dock line just for launching. One end is tied off in the middle off the boat. The other end goes through the jib jam cleat. This way I can hold the boat to the dock with a short adjustable loop. When I get ready to depart, its just a matter of pulling the line from the cleat and flipping it off the dock pole. All done from the cockpit, so I am only away from the outboard and the tiller for about 3 seconds. Bring it into the dock the same way. I've never understood why all boats don't have extra mid-ship dock cleats.