Fred,
Looking at the sailboat data pic it looks like your boat's keel is partially exposed even when winched up, just like on our Hunter. If that is the case then I agree it can be a chore to get the boat on the trailer properly, especially if your trailer has a tight keel slot you have to hit with the keel, like ours.
I re did our bunk boards on our trailer with new pressure treated 2x4 as that is what it was set up for. I made a long v front the inner boards to the outer boards to help guide the keel into the slot if you are just a bit off when you hit the trailer. This is what our trailer set up looks like.
The technique we have found works the best at our ramps, where we can't walk it in, is for me to back the trailer down and walk out on the trailer with the winch line out to the front of the bunk boards. Cindy drives the boat at a slow speed onto the trailer. She has gotten very good at hitting the keel slot and very seldom requires much correction from me to line her up. Once I can reach the bow eye on the boat I hook the boat with the winch line and winch her on the rest of the way. If it takes us longer than 2 minutes from start to finish it is because someone got in Cindy's way and she had to maneuver around them on her way into the trailer.
Knowing how far to back the trailer down into the water takes some trail and error. I like to just bury our trailer fenders. That still leaves enough of the keel slot for Cindy to sight on and yet enough exposed boards to act as a break and bring the boat to a stop.
The long v leading into the keel slot has really helped, you just want to be careful not to back it too far down into the water and have the v submerged below the keel, if that happens then the v is useless and it is easy to get the keel off to one side and out of the slot. the boat list about 10 degrees when that happens and we really have to back the trailer way down in the lake to get the boat to float up and over the bunk boards to fix that. It only happened once and that was before I added the long V. Don't want it to happen again.
Ramp activities can be one of the most stressful times of boating. Some advance planning and communication can go along way to make it as stress free as possible. If your boat does not have a bow eye on the leading edge of the bow then I bet you did have a heck of a time getting it on board your trailer. I would suggest adding one along with a winch stand and v bumper to the winch stead to pull the bow of the trailer up to. Hook a safety chain to the bow eye once you have the boat in place on the trailer, tie the both corners of the stern down to the trailer and you are good to go.
Good luck and hang in there. You will get it figured out.
Sam