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I was hoping to be able to open some old (DP5) files with the new windows version.
No can do.
Even an .omf file created with DP5 is no good when opened with DP8 windows. (only 1 out of 4 sequences, audio all over the shop.. no MIDI)
Is the partly because my mac DP is old, or is there no compatibility period?

Haven't tried it yet, but thinking about what the problems might be - it probably all comes down to file extensions. I don't believe DP5 was using file extensions at all, but I could be wrong on that (it's been a while). Now all the newer versions do, i.e. .dpdoc for the session, .wav, etc. If you still have a Mac, download the Mac demo and use that to convert to the newest formats. Old SD2 audio files from the Mac would prove to be more problematic because they store the headers in resource forks which the PC can't see. If/when you convert, you should probably convert any SD2 to WAV while you're at it. If you were using AIF (or WAV if it was available in DP5) files for your old session audio another thing you could try is to add the .aif (or .wav) extension to your audio files and the .dpdoc extension to the session file and see if that works, but don't have much faith.

Try to open it using LOAD.

Did any of those old DP sessions have Apple Audio Unit plugins in them by any chance?

I struggled with the same problem with some old Mac files from DP 4.6 on an old machine. Failed miserably until i just changed their file extensions by adding .dpdoc and they were even instantly recognized as DP files on the desktop by my new PC when I moved them. It didnt seem to make much difference whether I renamed them before or after moving them to a thumb-drive. DP8 opened them perfectly down to the tiniest detail.

HOWEVER - I HAD BETTER LUCK OPENING THEM FROM INSIDE DP than by doubleclicking them on the desktop, until I saved them once. DP hung up a couple of times whenI tried double-clicking