I'd suggest taking a closer look at the overnight schedules. DC to Chicago on the Capitol Limited works well -- it's a late afternoon, central, major city departure and an early enough central, major city arrival. Going the other way, it doesn't work so well -- you arrive DC in the afternoon, with most of a day gone.
It's the same with the Coast Starlight. Leaving from Seattle you'll lose a whole day getting to the Bay Area (half a day from Portland), and you'll likely still need time to connect to your final destination -- it doesn't go to San Francisco, and Silicon Valley is spread out all over the place. Not so much is within walking distance of the Oakland or San Jose stations. Coming north, it's the same problem in reverse, except even getting to Portland burns a whole day.
If he's thinking about optimising overnight city pairs for business travel, then it would make sense to break up the Starlight into two trains, one that would connect Portland and the Bay Area overnight, and a day train between the Bay Area and LA. Or maybe just move up the departure times from LA and Seattle -- a 6am departure out of LA would make the Bay Area to Portland run a little more workable, and arguably improve business service between LA and the Bay Area, or at least between the Central Coast and LA.
Then there's the on-time problem. You're absolutely right that it's critical. One way to address it is to make the runs shorter, i.e. break up or truncate the long haul routes.