Will I look like an idiot sending this?

Your best bet is to leave it be or your going to do more bad than good. You dont have to throw the things away which will lead you in good reason to contact him again in the future, or if after you do move and realise he wasnt worth your talents, at least your have a good feeling about throwing them away, but dont try and talk to him just because you miss him, you will only put yourself in a possition where you will wish you had never put yourself in, and yes, probably only to become their joke of the evening. His loss for being a **** if he loses his things and you, so dont you worry about it, just remember, your talents are what count, not his.