Not enough free space on iPad

I tend to travel a lot so when I am gone for long periods I sync my devices with my laptop but when I am home I prefer to use my desktop as it obviously has my entire library on it and not just a portion of it.
My problem occurs when I tell my iPad to sync to my system again. It will sync initially just fine but the second I try to add any major content to it (not music, apps or books) it gives me the error "not enough free space". Even if I erase all non-app content on the iPad and it tells me I have over 100GB of available space the second I try to add 7 movies I get the same error message.
All the "help" articles I have found seem to assume you don't actually have enough free space or just plain don't work.
I found one of the problems that may cause this is not having content on my laptop that exists on my iPad when I first try to sync it. For some reason this drives iTunes into an error it can't escape from even if you tell it to copy the content from your iPad.
The only way I have currently found around this is to do a full restore (not from a back-up) each time I bounce between machines which is of course a pain in the rear and takes a while.
Anyone have any suggestions on another way to fix the problem?

Using two machines is probably the issue. The ipad really wasn't designed to be synced to multiple machines.

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