As a graduation (grad school) present to myself, I'm planning on going to Glacier National Park (WGL) from BOS. The twist is that I also want to go to New Orleans, so I'm planning on taking NERegional to Crescent to City of New Orleans to Empire Builder. Of course, I'd stop in NOL for a couple days, enjoy the city, eat beignets, etc, so it's really more like "NERegional/Crescent" and "City of New Orleans/Empire Builder". I've read some of the amazingly informative posts on here and still have a couple questions:
1) Am I insane? To tell the truth, I have a kind of a hankering to go down from Seattle (finishing the Empire Builder line) to SAC and head back to Chicago on the Zephyr and return to Boston on the LSL. To make 4 connections- is that pushing my luck way too far, even if they're all a few (sometimes many) hours apart? I'm primarily concerned with SAC and CHI here, as while they're fine cities, they're only transfer points on this trip.
2) Has anyone recently used a USA Rail Pass on similar trips (long, multi-connection)? Do you know if it will cover late trains and missed connections, especially since it requires you to have made reservations for each leg beforehand? Since I'd like to visit these other cities and these other lines, I think the Rail Pass is the most effective use of my money instead of paying a total of 500+ without it.
Thank you so much in advance!
1) Am I insane? To tell the truth, I have a kind of a hankering to go down from Seattle (finishing the Empire Builder line) to SAC and head back to Chicago on the Zephyr and return to Boston on the LSL. To make 4 connections- is that pushing my luck way too far, even if they're all a few (sometimes many) hours apart? I'm primarily concerned with SAC and CHI here, as while they're fine cities, they're only transfer points on this trip.
2) Has anyone recently used a USA Rail Pass on similar trips (long, multi-connection)? Do you know if it will cover late trains and missed connections, especially since it requires you to have made reservations for each leg beforehand? Since I'd like to visit these other cities and these other lines, I think the Rail Pass is the most effective use of my money instead of paying a total of 500+ without it.
Thank you so much in advance!

Comments
I'd say you might want to look at Amtrak's on-time performance for each route and make decisions accordingly, noting that even a route with good performance can have a severe delay the day you're riding due to circumstances beyond Amtrak's (or even the host railroad's) control. My personal record for delays was 18.5 hours, but most have been six or less.
But it's a great route. Have fun!
End point arrivals *tend to be* more timely than mid-route arrivals. There's padding built into the schedule there, and often the last couple of stops are drop-off only so they are either very quick or may even be skipped altogether, if there's no one getting off. Your SAC stop is the one to worry about and allow extra time for. Six hours is *probably* okay, but the Zephyr is almost guaranteed to be on time at that point, and the Coaster is mid-trip and might not be. If you can find a reason to spend a night or two in the Bay area, that'll fix having much to worry about, and it'll be a nice break. You wanted to see Alcatraz anyway, right? (;