We have done a number of trips with Santana (~12), have enjoyed doing them while seeing some great locations. I agree that one of the reasons we have continued doing them is seeing previous participants on subsequent trips. I have had some frustration with logistics on some Santana trips and increasingly so but also have seen Bill go to great lengths to make something work for participants when things went pear-shaped as well as the behavior you have described.
That said, we have seen them get bigger with more participants which has changed the nature of the trips. In response we have been doing a number of trips with smaller numbers of participants with other tour operators(though not yet either Backroads or Trek) that seem to suit us better now and are not always limited by having to be on a boat. FWIW, Santana have offered mechanical support with support vehicles for a few years now but not to the level I have heard offered by Backroads especially.
FWIW, we received an email about a week ago from Santana saying that the April 2021 Portugal trip has not been postponed so my original comment still seems to be holding true. That Portugal is closed for US citizens was not mentioned. We are just waiting for the inevitable with Croisi and Santana coming to agreement to the new date. Like others, we are disappointed in how this continues to be handled but as people are continuing to book 2022 tours with them, albeit at a slower pace to sellout, we expect it not to change. We won't be committing to future Santana events under the current terms and conditions.