MWS, thank you for the detailed response. I agree that $250 is too much for shoes like that as I got my McAllister and Strand firsts for $249 and $229 during sales. I appreciate the info so that I know what to look for and the comment about repairing makes sense. Even if a cheaper shoe can be repaired, the poor quality upper will make it not worth it.
Based on cost-to-value, style and customer service, I lean towards AE but there are a few things I've seen in other brands that I like so the education on what to look for is helpful. I know this is an AE appreciation thread but if anyone knows where to try on Carmina, Meermin, Loake, Tricker's, etc. I'd love to know.
Sky Valet in Washington D.C. (Georgetown) has a decent assortment. Last time I was there, they had Carmina, Loake, Crockett & Jones, Alden, Edward Green, and a couple others. I don't remember seeing any Meermin or Tricker's there.