What mmitties said.
The key to getting back on the lift in a cross wind is when backing off the lift only lower the lift until the boat starts to float than power the boat off the lift with the big engine. When loading the bunks will catch the boat and prevent it from hitting hard against the guides.
A further enhancement is to have a remote control with an electric lift motor. Lower and glide out. Once out of this lift use your remote to bring up the lift carriage about 4-5 inches. When you come back in our boat will glide onto the lift but not too far. If you need to lower it a bit to get fully on use the remote and move forward.
We have been using an electric lift motor with a remote control for over 10 years. My daughter, son-in-law, son and wife can get the boat off and on smoothly. Even in rough water, because the boat goes onto the lift and is stable immediately and you can “fiddle” a bit to get it on exactly as you like if needed.
Another improvement when using a lift is to add a small triangular piece of dock to your main dock that you place where the bow sits on the lift. Everyone can board and get out of the bow area without have to crawl over gunnels or lift support braces from the side of the boat. Hopefully your Dad still goes out with you. This piece would help him immensely.