I've owned two samples of the 105/2.5 Ai-S, and three different 85mm f/2 models, two Ai, and two Ai-S. I bought the last 85mm, an f/2 Ai-S a few years back in immaculate condition, for a really low price; I took it out two years ago, and shot it on a walk around the neighborhood. I was shocked at how poor it was wide-open at f/2, but it was remarkably better stopped down to f/4.
In the mid-1980's I had an 85/2 Ai which developed very dry and squeaky focusing ring movement, which was common on that lens (squeaky focusing ring movement), and I replaced it with another 85/2 Ai in '88. The Ai-S lenses are actually _different_ than the Ai-S; the Ai lenses have non-linear diaphragm mechanisms, and typically have stiffer, longer-rotation focusing than the Ai-S models. The difference between an Ai lens and an Ai-S lens is also often seen in the lens barrel cosmetics. The Ai-S lenses have an almost feather-light focusing ring movement, while the earlier Ai generation lenses have much-stiffer, and slower, turning of the focusing ring. I prefer Ai-S lenses for these two reasons.
Take note: the 105/2.5 Ai used a screw-in lens hood, but the Ai-S 105/2.5 model has a built-in, sliding lens hood.
Anyway, great memories of both the 85/2 Ai and the 105/2.5 Ai-S. The 105 was the first "good lens" I bought brand-new, as a youngster, back in 1982; I payed something like $179.95 for the 105/2.5 Ai-S; this was at that time, sold to me as being a lens that offered the then pretty new CrC, or close-range correction. I STILL own that lens, and still shoot it occasionally. This is, hands down, one of the FINEST lenses Nikon ever released. This lens focuses superbly by hand and eye. It has a wonderful mix of focal length, maximum aperture, and focusing helicoid pitch that make this, in my opinion, the easiest-to-focus manual focus Nikkor ever made. In the 1980's this was my go-to lens. I cannot recommend this lens enough. BUY one! You most likely will really,really enjoy it.
In my opinion, the 85mm f/2 is an "average" imager....the lens has crappy lens character, both in the Ai and Ai-S eras...its images are just "Meh". The 105/2.5 on the other hand, is a beautiful imager. Wide-open it has a slightly dreamy look. Stopped down to f/3.5 to f/5.6, it's just awesome. At f/8 to f/11, it makes really great landscapes with deep depth of field. This was, I would say "the" lens focal length for general photography, from the 1960's to the start of the 1990's.
The 85mm focal length on full-frame is like a long normal lens, to me. The 105mm length is a true, short telephoto, and is selective in angle of view, and is long enough to start getting into blurred backgrounds in many situations, but is easier to use as a general-purpose lens than a longer tele like the then-popular 135mm f/2.8 models that were so common. Where a 135mm lens is TOO long in many indoor situations, the 105mm is more easily deployed in situations like speeches or in meeting rooms, etc. Again, the 105mm f/2.5 Ai-S has the newer-style short-throw focusing helicoid, and it's pretty much perfect for hand-focusing! It is a definite must-buy lens for anybody who likes manual focus Nikkor prime lenses. Take an asparagus bunch, blue rubber band, and slip that behind the rear edge of the sliding lens hood, and you'll create a shock-absorbing front setup, and protect the front element from bumps, and also eliminate the need to use the front lens cap when dropping the lens into the camera bag or backpack after having changed it out.