Kind of a trade off, digital is certainly better for learning and testing with quick reviews but solid darkroom printing does make you a better photographer as well, at least you have to edit harshly so you're not wasting your time printing the mediocre stuff.
The other thing is that by the late 1990s film was pretty fantastic. Look at how ISOs had been able to climb... when the Leica was introduced average film speed was equivalent to what, ISO 10? So I would hope that over the last twenty years we'd have fine grained ISO 800 film for everyday use.
I'd be quite happy with a Leica M provided they had faster shutter speeds, which I do not know if those would be feasible? (thinking not, you'd probably have to have a vertical shutter like a Nikon FM or F3?)
And I'd probably use larger formats to differentiate my work, I used to think shooting 4x5 handheld was cool but the reality was that a good medium format rangefinder like the Fuji 6x9 was usually the better choice. Just a few years ago I spent a Summer with a Fuji and the excellent ISO 3200 BW film and got great results.
I bet we'd have really wonderful Contax T5s and T6s, Ricoh GRs with functional LCDs, and Konica Hexars would be repairable.