I cannot answer all of those questions but my preference in shooting are fairly fast short to medium tele and long focal length lenses - especially those with "classic" optical designs such are Ernostar derivations / Sonnar etc : 75mm; 85mm/90mm; 105mm are my favorites. Of course I shoot normal and wide angle lenses when this is called for and some of them make pretty nice bokeh too - especially the standard lenses of course, but as it happens the above lenses are particularly adept at producing nice OOF imaging.
While I like good bokeh we all know it is somewhat situational - depending for example on the nature of the background and its distance from the point of focus. So I do not go"nuts" pursuing it though I am always gratified when I get it (Good bokeh that is - I very frequently shoot with open aperture so I always get some kind of bokeh.). In my "book" (as we say in Oz), though I very much like good bokeh, an interesting subject and sound composition are more important in producing a good image: I get bored "spitless" (see what I did there) looking at images, say, of flowers with soft bokeh in the background made just for the sake of producing soft bokeh. Though some people cannot seem to get enough of it. As far as I am concerned, I see too much of that kind of photograph, though not here at RFF fortunately.
Lenses in the class I mentioned above, that I have had good results with include the following (I can only speak of these as, although I would like to own every classic lens that takes my fancy, obviously I cannot - though my wife thinks I try. I am sure there are many many more than the ones listed below.
Voigtlander 75mm f1.8 Classic
Canon 85mm f 1.8 FL mount (Said to have the same optical design as the LTM version)
Nikon 85mm f1.4 (I only have the AF D version but it is excellent in this department)
Canon 100mm f2.8 chrome nose in FD mount.
Nikkor 105mm f2.5 (Rangefinder and early version of the F mount one)
Asahi Pentax 105mm f2.8 M42
I will not even get into 135mm lenses as there are too many here to mention. But I should say that there are any number of longer lenses which perform well in this department too- even the humble Asahi Pentax 135mm f3.5 can produce really nice bokeh (Due perhaps to its Sonnar design?). A couple of even longer lenses I can think of includes about any version of the Nikkor 200mm f4 (slowish but capable of excellent OOF results) and the Nikkor 180mm f1.8 (I can especially vouch for the early AF version which I own).
One thing I would be interested in hearing your response on, is something the guys over at Classic Lens Podcast described as "wet on wet" bokeh. Which I have to say is pretty sweet based on some images I have seen with the character they describe. Some people say it is just normal everyday good bokeh but true or not, in any event I rather like its "painterly" look - a bit like a watercolor.
Here is the Podcast link
https://www.classiclensespodcast.com/e/53-wet-on-wet-bokeh/
And here is a link to an article in which it is discussed, with samples provided:
https://tech.swiss-1.ch/wet-on-wet-bokeh/
The lens in the article above is a Raynox M42 135mm f2.8. As it happens, I have a very similar looking lens with another name which performs similarly to that in the article above (I forget the name and it is in storage and I do not have time to go hunting right now). I find this kind of bokeh attractive though the lens is not all that sharp wide open. Never the less it is OK in that department.
A final aside. I always used to get a smile (its a few years back now) and considerable enjoyment out of watching Kaiman Wong on DigitalRev's channel on youtube. In this video he goes out on a photo walk with "Garcia" a model who sometimes appeared as such on his videos and in this video does so in the capacity of an inexperienced photographer. The video compares the bokeh of the Leica Noctilux 50mm f0.95 and the Canon 50mm f1.2.
https://www.youtube.com/watch?time_continue=38&v=tWU8DpTo5kg&feature=emb_logo
And a slightly more serious effort here:
https://www.youtube.com/watch?v=tFJ96onYmu0