Patagonia
Is it a bad idea to contact my WL manager (from last year) who encouraged me to reapply to reiterate interest? I have a feeling I am again on the fence...
I'm pretty sure nothing good would come of this. They have already looked through your application and have almost definitely rendered a decision, you just don't know what it is yet. Only thing it would do is give you the opportunity to flub up the conversation or appear desparate, and then you'll feel like a complete idiot after.
Unless you have been keeping in touch with this person and think it wouldn't be weird to contact him/her right now.