Here are some options in a similar price range, but each with differences and/or disadvantages from the AE. This assumes you live in the US?
- Johnston and Murphy:
Georgetown captoe $375 (made in the US; a little more $ than AE; custom made): http://www.johnstonmurphy.com/product.aspx?c=1372&sc=1372&pid=21094
Hyde Park II $275 (probably made in India): http://www.johnstonmurphy.com/product.aspx?c=1372&sc=1372&pid=22178#tabProdInfo
- Loake (made in UK, so shipping, customs, and sizing are difficult)
- Meermin (made in China/Mallorca, Goodyear welted, shipping, customs, sizing, but good prices)
Those are what I can think of in the price range.
As for pants tailoring, you can certainly have them tapered. But you are probably better buying slimmer pants/suits to begin with.
I had been aware of J&M's Georgetown captoe just from seeing it online. The description of it seems to put it in the same quality realm as AE or Alden (give or take). The other day I went into a brick and mortar and asked if they had one I could look at. The salesman just looked at me and said, "no." Then he paused for a second and said "We may have one in the back if you want to see one." I said I would like to see it so that I could compare it's quality to the next tier captoes (which are the Hyde Park II you mentioned above), and are always out on the sales floor, and they are definitely made in India. The guy went back and brought out a Georgetown for me to examine. Appearance wise, I would place it in the Alden or perhaps Crockett & Jones realm for upper and welt finishing. The sole is still stitched-aloft rather than closed-channeled. They had a more beveled waist, reminiscent of a fiddle-back waist seen on extremely high end shoes, but it wasn't quite there. It pretty much looked identical to an Alden or AE sole with a sculpted waist. The sole edge and welt was definitely cleaner than what you see on a Park Avenue. The leather upper quality was on par with Alden or AE. They have a half socklining just like Alden and most English made Goodyear-welted shoes.
I noticed an interesting statistic on J&M's website where they say that it takes 115 steps to manufacter these shoes. All of the other Goodyear-welted shoes claim that it takes approximately 200 steps (Allen Edmonds reports 212, John Lobb reports 190, all the others that I know of fall into this general area give or take). I wonder how J&M is trimming off so many steps? What are they leaving out? Obviously these are a hollow echo of the former J&M Crown Aristocraft shoes that were made decades ago, but they seem like an ok choice for what they are.
Anyway, I just found it interesting and thought I'd mention my observations for what they are worth.