Cross Check feedback
Ryan- I'm in lot of the same places as you on the choices, wanted to chime in with my experience. I recently picked up a 54cm Cross Check w/ a Straggler fork (disk and lots of braze-ons), very well setup as 2x9 w/ beefy wheels. Found on the local CL for $250, pretty much a steal. Added racks and fenders, just did 330+ gravel miles over 8 days on it. Impressions- bike is very versatile, but also _very_ heavy. I had to start deciding which things to leave off due to weight w/ full bags. My ride was flat (GAP/ C&O Canal), I wouldn't have wanted to climb anything with it loaded. All in all a good way to get started, but it's not my endpoint.
Hope this helps.