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It probably only gets faster later because it has publish cache and the compiler is already in cached memory after you've run it the first time. For the same reason the second time you launch Flash after a crash it loads much faster as well (cached in RAM).
Can't say why you're getting the crashing in general but have you tested just publishing the whole FLA as a SWF to see if you get consistent crashes as well? It seems something isn't happy the first time you invoke the compiler.
Yes, it's pretty consistent about speeding up after another attempt. All other export functionality is instantaneous and don't cause issues. As an experiment, instead of force quitting Flash I just waited a long time and the Export does eventually go through. Susbsequent attempts are quick and painless.
Flash CS5.5 is also installed on this machine. Would that be causing any sort of cache/compiler interference?
I think I may have stumbled upon a solution. I have Sophos AnitVirus, so I went into the On Access Scanning options and added all my Adobe application folders to the Excluded list. Seems to be functioning well now. Even after restart.
That probably was your issue. Everything in memory is being filtered and quite a bit goes through while you compile.
The speed up on subsequent exports is most likely due to what I already mentioned, RAM cache and publish cache. That's the reason there's a function to delete the ASO cache. If you want to determine if that's the reason it's exporting much faster a second time, delete the cache and export again, see if it takes a long time. The function is in the menu Control -> Clear Publish Cache.