The old style, VO randonneur racks are much more confidence inspiring. They have a stud that passes through the fender mount in addition to attachments at the cantilever mounts. No idea where you'd get one now though. Was going to their site to provide you a link and I see they've gone cheap with center of the fork attachment, and also bumped the price up. I do like the idea of having the side-supports at the canti mounts, so you won't have multiple attachments at the same point and possibly conspiring to loosen the securing bolt. My other main concern was the apparent downhill slope of the rack - which you have explained is an artifact of the angle it was photographed at, so never mind on that.

It also looks like your right front brake pad might catch the slightest bit of your tire, and the length of the bolt behind the right dropout that secures your low rider and fender stay is a little bit longer than ideal.