The big thing the Cross Check has going for it is the Campy components. People seem to fall into two groups with regard to Campy: (1) love it, (2) don't really think much about it. The fact that there doesn't seem to be a "hate it" group says something, but personally I fall into the second group.

The two chief complaints people have with Cross Checks are (1) they're heavy and (2) the head tube is too short relative to the top tube. The first complaint is really misplaced IMO. The frame and fork weigh maybe a pound more than other framesets in the same price range. The weight generally comes from the components, and again is limited by price range. The head tube issue is the main reason I no longer own a Cross Check. I had one for three years, and it was a good bike, but I liked the geometry less than that of my other bikes, so when it came time to sell one the Cross Check went. It's designed like a road bike with a high bottom bracket more so than like a traditional CX bike. (The Outlaw, BTW, looks like it might also fit that way, but they don't specify enough geometry for me to be sure.) If you've ridden the Cross Check and you like it, then that's not an issue.

The great thing about the Cross Check is that you can do nearly anything with it: single speed, IGH, light touring, commuting, CX racing. It is the proverbial "jack of all trades, master of none" bike.

I don't know a lot about the TriCross, but I don't think there's anything hidden there. It is what you see. The 9-speed Tiagra components weren't bad, but 10-speed Tiagra is definitely nicer.

For the same price as the Outlaw, you can get an Airbourne Delta. It's a very similar bike but comes with Apex rather than Tiagra components. It also has BB30 bottom bracket (which gives you an option for single speed down the road if you like) and a slightly better crankset. Shimano vs. SRAM is a personal preference, but most people seem to view Apex as being more on par with 105 than Tiagra. I think the Delta has better geometry for CX than the Outlaw, but for commuting either would be fine.