The web consensus seems to be that shoes like this are perfectly fine to buy used. The only downside is, after a year or two the previous owner has broken in the sole to fit their foot. Since you're probably resoling relatively soon, that's acceptable. Ebay, or a another used shoe marketplace (
http://www.shermanbrothers.com/catalog.php?BrandCode=AL), is the way to go. That means you need to know what you're looking for, and know your sizing on both length and width. You accept a bit of risk on size, since not all shoe lasts (the chassis, essentially) are exactly identical.
Online reviews point to generally low quality in Johnston & Murphy.
I'll stop into Alden probably Thursday. I have my eye on their 'George' chukkas, if I can find them in black and at something like this sale price (
http://leffot.com/shop/index.php/shoes/alden/91672-george-boot.html).
Reasons for Alden:
Their shell cordovan (horse leather) and construction are widely praised
They last. Many forum posters had 8-12 year old shoes of this brand, and mentioned resoling every 2-3 years.
They are more functional than fashionable, as dress shoes go
They require less polishing-type maintenance than cow leather shoes
Against:
$500 is still a lot for shoes, even if we're avoiding the $800 Prada
Allen Edmonds is the next brand that comes up, at least in the <$1k price range. If I opt for a cow leather shoe, it will probably be one of theirs. Compared to Alden, you get like -$100 to 150, and -2-4 years of life. Most of this is due to the difference in leather type. Horse leather is essentially waterproof, but harder to come by since it's illegal to slaughter horses just for their leather.
Aside from Chukkas, Park Avenues or Oxfords also fit the style I'm looking for. Personal preference: Bluchers are boring and wingtips are gaudy. YMMV.