The Canon 85mm f/2 Serenar is a good and eminently usable lens.
As far as comparisons are concerned, I have both a second-version Canon 85mm f/1.9 LTM and a Nikkor 85mm f/2 LTM, so I can comment based on personal experience with using them. (I also have a current-production Leica 75mm f/2 in M-mount, so I know how the older lenses compare with current Leica glass.) I once owned a newer Canon 85mm f/1.8 LTM, but it had been improperly serviced at some point and would no longer focus accurately, so I cannot offer any comments on that lens. It was a limited production lens and is relatively scarce, so prices reflect collectable value as well as useful performance.
The Nikkor and Canon lenses have the same focal length and similar maximum apertures. In general, the similarities outweigh the differences, and both can be used effectively for portraiture and available-light shooting. There are some differences, though, including the following:
• When shooting at maximum aperture, the Nikkor 85mm f/2 LTM yields higher sharpness and contrast than than the Canon 85mm f/1.9 LTM, although it is a matter of degree and the Canon is reasonably good. The second-series Canon 85mm f/1.9 LTM, which came out in 1958, may also be a bit better than the slightly older Canon 85mm f/2 Serenar LTM, which originally came out in 1948, as the lens was redesigned slightly and there were advances in lens coatings during the decade between the two versions. For what it's worth, the Canon 85mm f/1.8 LTM, which came out in 1961, had a reputation for having optical quality at full aperture superior to that of either the Nikkor or the older Canon.
• At medium apertures such as f/5.6 or f/8, the optical performance of the Canon 85mm f/1.9 LTM improves considerably, and is noticeably better than its optical performance at maximum aperture. It offers very good optical performance for daytime photography at medium apertures.
• When shooting against intense light sources within the image area, the Nikkor is less susceptible to flare and ghosting than the Canon. In my experience, the Canon 85mm f/1.9 LTM flares quite a bit and produces noticeable ghost images when shooting under these circumstances. Basically, there have been a number of advances in the field of optical engineering in the half-century since the Canon was designed and built, and this is one of the areas in which progress has been noticeable. There are occasions, though, when the flare and ghosting can be used intentionally for visual effect in an image, so the technical deficiency of the old lens can sometimes be an artistic advantage.
• There are also handling differences between the lenses. The Nikkor is shorter in physical length, and balances noticeably better on a Leica body, than the Canon, which is relatively long and front-heavy. When shooting with the Canon, one supports the equipment at a balance point under the lens rather than under the camera body, as would typically be the case when shooting with a telephoto lens on an SLR. Again, the differences are a matter of degree, and the Canon is not bad in this regard; the Nikkor is just somewhat better.
• As between the old Nikkor 85mm f/2 LTM and the Canon 85mm f/1.9 LTM, I would choose the Nikkor over the Canon as offering somewhat better optical quality at maximum aperture, especially with any light sources in the image area, and somewhat better handling characteristics. The differences are not all that great, though, and the two lenses are in the same general ballpark.
In summary, the Canon 85mm f/1.9 LTMis a good and eminently usable lens for portraiture, available-light photography and daytime shooting, as long as one keeps its performance characteristics in mind and avoids shooting into direct light sources when possible. It may not be quite as good as the Nikkor, and is definitely not as good as current-production Leica lenses, but it is surprisingly good for a relatively affordable piece of used equipment.