Just When is it Finally Time to Upgrade?

This photo is from 2011. I had been riding this bike 15 years by then. And I'm still riding this bike today, a Trek 2120. Early carbon technology that's still intact 30 years later. Somewhere along the line I destroyed the original front fork in a crash. And the caliper brakes are the only part of the Ultegra group that still remain. I'm pretty sure I'm the butt of a joke every time I roll it into a bike shop for service.
But now I'm approaching 71 years of age and finally coming around to, maybe it's time for a new road bike. I think I've earned it by now. And no, there's no way I'm going to spend 4 or 5K. That's just too much money for a bike that 's used mostly for occasional 30 mile recreational rides.
– I don't want to be tucked into a racing position for very long, my hands are on top of the bars most of the time.
– I ride solo or maybe with a friend or two. No big group rides. No rush to get there.
– I'm hardly ever going to leave the pavement for gravel
– I'd love to have disc brakes
– Where I live, sometimes the pavement sucks.
– I hate fixing flats on the road (but who doesn't)
Anyway, it feels like bike tech has come a long way since the 90s and it's time to take the plunge.
With some research, I landed on a Cervelo Caledonia 105 as a likely candiate. But I've never seen one or ridden one. Another candidate: the Canyon Endurance Allroad, what seems to be a very nice Aluminum frame and decent group for $1500. Again, never have seen one in the wild.
Coming off the Trek, would I be happy with one of these bikes? Is there something else I should consider? Or should I just keep riding the 2120 unit it stops? Or until I stop? At this point I'm not sure what will happen first.