As regards the second question: I've never heard of a by proxy baptism. If your son is baptized by an Anglican, then he's Anglican. If he's baptized by a Catholic, then he's Catholic. Accordingly, the only way to be baptized Orthodox is to be baptized by Orthodox clergy in an Orthodox Church. I've never heard that anything different was ever permitted, but I could be wrong, especially considering that this is your child, and not you, whom you want baptized.
However, if one looks at this in the light of much, though certainly not all, of Orthodoxy's willingness to receive other baptisms as "valid upon Chrismation," then I see a loophole in the above idea. But, considering that the Orthodox Church considers only her baptism effective in and of itself and considers others ineffective until given grace retroactively upon Chrismation, I'm not sure you would want to knowingly give your son an ineffective (a.k.a. invalid) baptism, nor do I think the Church would bless you to have him so baptized, knowing that you knew it was invalid.
Again, I don't know how the Church would view your specific situation--only your local bishop can make the decision, and I'm glad I'm not him (for other unrelated reasons). All I shared with you above can only be considered vague generalities based on my limited understanding of our canonical tradition.