Let's see if we can deal with each of your issues, in order.
First, the Tojiro DP and the Tojiro DP Cobalt are literally the same knife - just a different way of describing the core steel. Probably different writers on different web sites, or different automatic translation software.
Microchipping on any VG-10 steel knife edge is always an issue, but it's a matter of priorities. That's just part of the difference between Western knives and Japanese knives. Western mass market knive companies want knives which will not chip. So, they make the blades tougher. The way to do that is to heat treat the steel so it is less likely to break, and will instead deform. Japanese knife makers are more interested in getting and holding a sharp edge. So, they heat-treat the knife to be harder. However, that makes the steel comparatively more brittle. Take your pick, but upper-end Japanese knives are just easier to sharpen and will resist losing the edge all that much better than the tougher-steel western mass market knives. For what it's worth, the Tojiro DP is thought to have much less chipping problems than other VG-10 steel knives.
The anti-stick MAC knife you are referring to is the BSC-85, a resin-coated blade, and is made for sushi chefs. It is limited to a single length, 8-1/2 inches (210 mm), and MAC-USA says it is a coated version of the HB-85. I suspect the resin coating might not last all that long, since it is listed as non-dishwasher safe by Amazon. One former expert participant on ChefTalk, BDL, referred to the MAC Chef line gyuto's as "whippy". I have never held one, so I can't say one way or another, but considering the light weight of knives in the Chef series, they very well might be extremely flexible.
The Richmond Artifex is not so much a "bad" knife, as one in which the manufacturing process is simplified so as to keep prices down. It may not be at the quality level of the Tojiro DP or certainly any of the MAC's, but it is certainly better in performance than any Wustie or Henckels (excepting Japanese-made ones).
The two options you list, the Hiromoto Aogami Super Steel (usually referred to on a number of knifenut web sites as the "Hiromoto AS") and the Hiromoto Gingami No. 3 (usually referred to as the "Hiromoto G3") are both considered as quality knives, though fit and finish may not be as high as other Japanese knives. The AS is a clad steel blade, with an inner core made of Aogami Super Steel, a high carbon, low chromium blade, which is much more reactive than any stainless. It can be brought to a much higher sharpness level than stainless steel knives, though it requires IMMEDIATE cleaning attention after being used. The G3 knife is a stainless monosteel (non-clad) blade which is also considered a good knife, though it cannot be brought to the same level of sharpness than the AS. Both are good, but attract different audiences.
Keep in mind that "stainless" does not mean "stainfree" - it means that there is less chance for the steel to rust. All steels develop oxidized surfaces - that's just the nature of steel and other iron compounds. It's a question of what type of oxidation. "Stainless" steel has a high level of chromium. That chromium on the surface of a blade will readily combine with oxygen and form chromium oxide. That chromium oxide layer will prevent the surface iron from oxidizing - hence it will "stain less".
Be advised that I am not a fan of Damascus. There is precisely ZERO performance difference between laminated blades with 3 layers and laminated blades with mucho-mucho layering. Beyond a single pair of outer layering and a core steel ("san mai"), you are paying for appearance and nothing else. BDL famously disliked all laminated blades and openly preferred a monosteel blade, because he perceived a more accurate feel of the blade when cutting. And once a Damascus blade gets scratched - it's a ROYAL PITA to restore the laminated look. No thanks on my part - I prefer a working tool, instead of something that I will be afraid to use for fear of damage. I may not be as fanatical about monosteel as BDL, but I prefer an honest, working tool appearance.
But, then, it's your money and your preferences, in the long run.
Hope that helps