CR had a lot of “being at the right place and time” moments, and from certain insiders I’ve talked to they certainly weren’t the first to try to convince the Japanese side to do streaming (I’ve heard that Funi pitched it to the Japanese even earlier). Why CR got through in the end though is basically the following points:
1) they had a large chuck of VC money to burn
2) they were an established internet site with proven traffic, hot on the heals of the Youtube and Nicodouga accqusitions (whereas the other licensors weren’t)
3) follow from above, Gonzo bought into them (the other licensors weren’t up for grabs, and they weren’t hot internet stocks, which makes them lesser of a return of investment, business investment wise)
4) they were American (yes, it matters, I’ve heard from contacts the Japanese wants to offer the Americans first dips because they are the still the largest non-Japanese anime sector, revenue wise)

It’s not a matter of the licensors didn’t try (which I know for a fact), it’s just they are in a different position to negotiate with the licensees. And if you are just pitching the whole streaming idea, than yes, I would say it is a bit naive because the devil is in the details as the idea of streaming media goes way back and the licensors, AFAIK, had all tried pitching it.