Lenses analyzed to death... Yes, that's very true. I have no experience with OM glass, only Nikkors (ans Contax/Zeiss; don't really see why that would be prohibitively more expensive) and find f.i. the 2.0/85 Ai-S gives beautiful portrait results in b&w. But so do the 2.8 and 1.4/85 Sonnar and Planar, albeit in a different way (the Nikkor appears to render a bit harsher).
There is of course also a difference in size, weight and handling of the bodies. I found OM bodies to be too small for my medium sized hands, and didn't like the sutterspeed ring as opposed to a dial. But that's all personal preference; you have to try for yourself.
my humble suggestion would be to start easy:
OM1 or 2 with 35 and 85
FM2 or FE2 with 35 and 85
RTS or RTSII with 35 and 85
Take all lenses with 2.0 or 2.8. You save a lot that way, weight. And money wise.
Let us know what you do!