[whpalmer4]

Even if it is checking many files, the behavior you report doesn't sound right. Let's say it has to read every file in its entirety, and then shovel an equal sized file back — that ought to only be doubling the time, plus a bit extra for overhead. Let's be generous and say the overhead is as much as it is to transfer the file — you still don't get anywhere near the times you are reporting.

What happens if you duplicate your outline on the Mac, and send the duplicate to the iPad, then update it without removing the previous version? I'm suspicious that perhaps you have a hard disk problem lurking here, and a copy of the file made on a different set of disk blocks won't display this issue.