Thanks for your detailed replies!
It actually seems like while the L&C does join the TM through the Lochsa River valley, it has an alternative route that user John followed, which diverges into a mountainous path pretty early after Lolo, both reconnecting at Kamiah. However, I got pretty convinced that I should stick with the TM until after the McKenzie Pass, which sounds awesome.
I would still like to visit Portland and reach Astoria before proceeding south. Another route that enables both goals, other than L&C, is to join the Cascades route after the McKenzie Pass, going through Mt Hood before entering Portland. Although Mt Hood sounds exciting, it's a long and remote path to take. Maybe I should make the choice en route to the area.
The Chicago to NYC idea is splendid.
The whole trip I believe would take about 100-120 days, starting late July until early November. I do not plan to hurry until after visiting DC, to allow a proper look around at NYC and Washington. I think early September is a reasonable time to reach Colorado. Switching to an easier pace on the Rocky part, I hope to reach Astoria mid-October. A quick ride down the Pacific coast should allow me to conclude the trip at LA, or SF if short in time.
I have no previous experience at touring biking, as I usually ride intensive day trips on a mountain bike. I don't worry about my physical fitness which is good, but rather about my ability to estimate the time correctly for that kind of an odyssey. I would welcome an expert opinion here
