Question here. For your case 1, is Captivate open still? Perhaps with that project loaded? I've seen it where things get really wonky if you work that way. It's as if Captivate still has some hooks in the project even after it has generated the output files.
If that's what you are doing, you might try closing Captivate and see if the crashing stops.
Additionally, it's worth noting that when Captivate creates the output files and you import them as Baggage into RoboHelp, the HTML file Captivate creates will have different coding than you will see if you simply insert a Captivate SWF into a topic.
Apologies in advance if you already knew any of this, but here is my own criteria for co-mingling Captivate with RoboHelp.
If I have a RoboHelp topic that has other information inside and I want that Captivate demo to be viewed right from inside the topic, I'll just insert the SWF. But if that Captivate demo is so large that it really warrants full screen viewing, I'll likely import the files as Baggage and establish a link that points to the Captivate HTML page to open things up.
Not sure if I've managed to actually help here. But hopefully I've done no harm.
Your comment about closing Captivate is helpful. I saw the same comment elsewhere on this forum, in regard to the same type of problem. I'll experiment to see if the RH crashes correlate with whether Captivate is running and what files Captivate has open.
Very interesting to know that you are using the same baggage file means of displaying Captivate SWFs that I am using in CASE 1 above. I was thinking that using baggage files instead of Insert>Adobe Captivate Demo was likely to be the cause of my crashes.