From what I gather from all the responses there are several factors that effect the series rating all of which must be proven by testing. The general consensus seems to be that with series ratings the upstream breaker will always trip first so that the downstream breaker is never actually interrupting the fault but is rather "withstanding it."
It sounds like the upstream breaker doesn't really "limit" the fault current to the downstream breaker but rather will either open quicker so that the downstream breaker does not interrupt, or take advantage of both upstream and downstream breaker contacts starting to part this being able to better extinguish the arc however the upstream breaker will still trip first? Or am I incorrect here and the downstream breaker may actually trip first in some cases?
Yep. That's how I see it works. The main concern is when the breaker contacts part and the existing breaker isn't rated to interrupt the fault level. That is the reason why addition of a series breaker was allowed in the NEC; to provide a leeway for existing installations with fault levels rising beyond the original levels of fault due to additions/ upgrading of supply transformers. The combination need to be listed as "series-rated" and you're good to go.