Thanks for the fine review. It seems like the main thing WINMOR wants to add is the ability to switch the data rate on its own, going faster when conditions are good and slowing down when they are bad. This is something Clover tried to do, but apparently was imperfectly implemented and hasn't been worked on in years.
So maybe we need to ask the fldigi developers for some hooks into the program that would allow changing modes on the fly, perhaps using RSID to let the receiving station know what is going on. That makes me wonder about PSKmail, which I haven't tried yet. I see a message just after yours that someone's server is going to be running THOR. I wonder if I could be trying all day to connect to a PSKmail server and failing because I don't know which mode it is expecting. Is there some provision for using RSID and beaconing to announce its presence and the mode it expects?