@drtdkidd
First, I am older than you trying to help fellow sailors without remuneration as God was good to me when I closed my business. It helped me when you responded.
First, I was a MacGregor dealer and was considered one of their largest dealers and knew their mast raise system. I also was a Catalina dealer helping with their mast raise system for the 250 and sport 22. As for the Hunter mast raise, there is a written write up by me found under boat info on the Hunter 26 which is applicable for the 19 as well. There are suggestions that would help you to know that would help you.
As for raising the mast, the 19 is a water ballast; thus, the center of gravity is higher versus the wing bulb keel on the 18.5 which is lower. The 19 would be more unstable if trying to walk it up versus using the supplied mast raising gear.
The trailer for the 18.5 with a wing bulb keel was poorly designed as it was a bear to load and unload.
I was concerned about sales because of that as the wings and bulb would catch on the trailer. Before going any further, can you take some photos of your boat on the trailer with emphasis at the keel guides, not the upright poles and post them here.
Dave