[Ken Case]

Originally Posted by rogbar

The only thing I can think of is that my outline has dozens of attachments - PDFs, audio files, image files, etc. I'm wondering if OO is comparing everything in the file to see what it needs to update and what it doesn't, and that comparing a bunch of large attachments is what slows it down.

OmniOutliner isn't involved in iTunes sync at all: it all happens behind the scenes down in the underlying operating system. (If OmniOutliner happens to be running, it's supposed to get notified about any documents which were updated so it can refresh its list of files—but that happens after the transfer finishes.)

Your speculation as to what's making it slow sounds reasonable. Also, I've noticed in general that iOS can be very slow to access files in a directory which contains a lot of individual files. (This usually starts to get noticable this when the count gets over one hundred.) By deleting your document first, you're guaranteed that the first hundred or so attachments in your document won't hit that slowdown (since the directory will start out empty).