Yeah, it is pretty competitive with a lot of changes recently.
I would get something that takes 40mm tires - if you want to go fast you can always get a second wheelset with ~30mm road tires.
Most people that go off pavement use tubeless ties. Have you researched that?
Then there are the tradeoffs:
- Do you want endurance or Aero fit?
- Do you want agile or stable?
- Do you want comfort or responsiveness?
I ride my bike a little like a mountain bike - much more aggressively than a roadie. I like a higher bottom bracket for pedal and chain ring clearance and for acceleration. But a low BB tends to be more stable on fast loose downhills.
Short rear chain stays tend to give better acceleration, while longer chain-stays can be better for long steady power, or backpacking.
The head tube angle (specifically the trail) is going to determine how agile the bike acts
The checkpoint is interesting in that it has a relatively short trail and relatively long wheelbase. The steering is pretty precise - sounds like you would rather have comfort over precision.
The bikes you are looking at are pretty competitive - but the most important thing is that the shop works with you to dial in the fit. A good shop will measure your inseam, and make sure you have the body angle and reach (stack & reach) to make sure your hands are in the right position and that you are comfortable.
Sounds like you like the Diverge. ;-)