Perhaps the best US Amtrak route is the Cascades, which runs from Eugene to Vancouver. It’s pretty slow once you cross the border into Canada, but the coaches are very clean and the stations are as well.
I prefer a simple ballistic nylon Tumi that only holds 4 credit cards and a drivers’ license in the middle. I’ve used a monogrammed silver billfold from Tiffany since I graduated.
Fortunately, my primary care physician treats me like a concierge doc, so no need for the extra expense now. He’s also in his 30’s, so should be around a lot longer.