Hi Andy,
Welcome to the Maxon developers forum and its community, it is great to have you with us!
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About your First QuestionYes, unfortunately it's not possible to catch the "hover" event as there's no such event. So yes, you're right, you can somehow emulate the desired behavior.
The suggestion for that would be to work with Core Messages, namely do your stuff (i.e. change the mode) as a reaction on catching the EVMSG_CHANGE message.
For checking the selections part, you can refer to the DunHou's pointer to the Ferdinand's script.
Cheers,
Ilia