Interesting info, John, I'd not heard that about Encore before. But I can tell you from personal experience that I've run exports of timelines much more complicated than the OP's, with CRAZY long file names--like a full sentance long--and not had an issue, using PPro CS3, CS4, and CS5.
To the OP: I'm wondering if you're experiencing some instability with your OC'd CPU? Try bringing it back down to stock and see if it still crashes on you...
I always have short paths and file names so have never had any problems... but did read/save those discussions of other people that DID have problems with long file names or "odd" characters in the name
Just one more data point to work on for troubleshooting
Can't hurt to test with shorter file names. I do not recall this being an issue for Premiere. And many users appear to not have problems in Encore despite ridiculous filenames and paths. BUT there were issues in Encore where shortening (or probably more importantly removing spaces or odd characters) fixed problems. So in Encore, "best practices" include short names/no spaces. I think the speculation was that it was the Sonic authorcore in Encore that was ultimately at issue; that's the other reason I suspect it is not an issue in Premiere. But if some poor soul with a problem doesn't test it, we'll never know!
It was Neil Wilkes, who offered up a list of "no-no's" in Encore, and did the follow up to point out that these issues exist in Sonic Scenarist, hence his assertion that it was most likely a limitation in the AuthorCore modules.
As for PrPro, one of the first things that I would look for would be gaps. CS5 has added a "gap finder" tool (this is not a GPS app. to locate GAP store locations). The Error Compiling... is common with gaps, as is the "Failure to Return Frame" in Encore's Transcoding. Might not be the issue here, but when one mentions "complicated," the opportunity does exist for a gap in the Video to be present.
Just a thought,