I've bought new AE on sale for $220. Close enough? If not, there are other options. You don't really need to buy used. Opinions vary, but I can't imagine anyone here really wants to buy shoes that have been broken in on another dude's feet.
I think it looks good. Most here on MC are vehemently opposed to shorter jackets, but I don't think we all need to go full-on traditionalist here. Sleeves do need to be a little longer, though, and I think your shirt cuffs need to be shorter (which is making it all look worse than it really is).