Article: Travel Insurance and Amtrak

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That said, I always purchase our travel insurance separate from the carrier (Amtrak, cruiseline, etc.), NOT through carrier at the time of booking/purchase.

I do that as well. Usually, the coverage from an insurance company different from the carrier is more comprehensive than what the carrier offers. I have had to use my insurance from time to time. If I had not had insurance, the money I would have lost would have negatively impacted my ability to take more trips.
 
I usually fall back on the coverage through my main travel credit card. The coverage there is greater ($500 vs $150; $150 wouldn't cover a hotel for a blown connection to the Cardinal, for example) and I don't have to pay anything "extra" for it.
 
I was able to collect on a claim with Allianz due to cancelling a flight Reservation to Europe this year. It's sort of iffy as to the terms. Anything less than an unexpected illness without preexisting conditions to yourself or travelling partner may create problems with a refund.
 
Travel insurance is a very individual matter. Each of us has different circumstances. Some coverage is afforded by certain credit cards. Do you have insurance coverage away from home? Health care in foreign countries is often not covered. I'm pretty luck, my coverage is worldwide, so I only have to consider possible medivac costs. Risk versus ability to absorb losses is a big issue. It is very easy and tempting to click yes on a pre packaged offering, but it may be much better to "customize" coverage, some of the companies that sell packages with carriers, also sell separately.
 
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