Thank you so much for your insightful response!

Yes, I am starting to realize, that what I actually need is not a cyclocross bike, but a gravel bike. Specialized has Diverge at several different price points and setups.

One of the shops has suggested that if I cannot find a gravel bike that fits (for instance, Diverge at the smallest WSD size of 48 might not clear the standover) they can put a more substantial tire on a Specialized Ruby with disk breaks. Basically, he said that as long as the bike can take a 32 tire with a good grip, it it much easier to fit me into it.

The problem I am having is that the shops in my city have very little selection in stock, and everything I want to even try needs to be brought in (I simply do not want the pressure of feeling that I have to buy), but going to Toronto to a much larger store is not a problem.

I put 105 and disks as a must. Five years ago I bought more bike that I really needed, but I enjoyed it and never felt the need to upgrade.