hey @Rob!
re 1), the way you’ve done it is prob the way to go to keep it as automated as possible. if you wanna go the more manual route like @Reynold_Chan did for the currently bundled structural stuff, you’ll need to do a bit of crafting to adapt to python as you’re totally right that the structure doesn’t always translate well from c# to py
good catch re 2) - i guess we aren’t supporting enums so I will have a test and add handling for that. super soz about that and thanks for bringing this to my attention! re the commit you linked - it’s just a change from SpeckleException to a warning so that is an unrelated issue and is not the cause of this. the serialisation logic hasn’t actually changed so if the enum serialisation isn’t working now, it was never working - oooops 
i’ve asked the lovely @Reynold_Chan to add some unit tests for the structural py stuff to make sure we don’t have any other bugs hiding there and to prevent stuff like this from slipping under the radar in the future!