I went 85mm (for fast prime), but that is because 100mm was taken for my macro lens. I couldn't see having the 100mm macro and the 100mm f/2 (when the 85mm would do).
If it is a FL you like, then yes it can make sense to have both.
Obvious a there are those who for FF want the Canon prime trinity 35L, 85L, and 135L. There is also the 35mm f/2, 85mm f/1.8, and 135mm f/2.8 SF for a poorman's version.
Some like the 24L, 50L, and the 100L (or f/2).
IMO a triplet of primes to use is very specific to the shooter. I also don't think that prime lenses have to be in triplet sets.
I think you should get the FL you use. Also the ones you can afford, as the Canon trinity would cost $4700+.
To me I like your second group (35, 50, 100) better with the 100mm being a macro. Eventually though I'd want a fast prime around there too.