iPad claims not enough space to sync files from iTunes when there is?

*sigh* I always dread trying to sync my iPad with iTunes on my Mac.

It's always the same old problems, and I just can't figure out why.

Here's a brief runthrough of the problem, using today's experience as an example:

I plug my iPad into my Mac.

iTunes says there is approximately 1.04 gigabytes of empty space on my iPad (in the capacity bar at the bottom of the summary tab).

This is reflected in the Settings of my iPad, under the General > Usage section.

I do an initial sync without changing anything just to update playcounts, etc.

It all goes fine, no errors.

I check two video files in my iTunes list that I want copied across, both approximately the same size, around 75 megabytes each.

(I have "sync only checked songs and videos" checked on my main summary tab).

Before I re-sync, I notice the capacity bar at the bottom of the summary tab has updated to now show 0.89 gigabytes of empty space on my iPad.

I then attempt to re-sync my iPad to get the two new videos copied across.

The sync does not work. I get an error saying that there is not enough free space, etc. An additional 146.5 MBs is required.

What?

Anyway...

So I uncheck one of the two files above, and the capacity bar now shows 0.95 gigabytes of empty space.

I attempt to re-sync.

This does work - just to prove that the syncing process does work.

I go back and check the second file and attempt to resync.

The sync does not work. I get an error saying that there is not enough free space, etc. An additional 77.9 MBs is required.

This in itself is confusing and frustrating, but it gets worse...

So now I go back and uncheck both files. I also manually delete from my iPad the file that had copied across before.

So now I'm back at square one.

I start the process again.

I only check one video file to copy across - the same one that had worked fine before.

I attempt to re-sync.

The sync does not work. I get an error saying that there is not enough free space, etc. An additional 70.1 MBs is required.

What the...?!

This worked fine just a second ago...

What makes this even weirder is that before all of this, before I even plugged my iPad into my Mac, I manually deleted about SIX videos off the iPad (that were then unchecked in iTunes before plugging in the iPad), again, all approximately the same size, around 75 megabytes each.

So if I can take six 75MB videos off the iPad, why can't I put two 75MB videos back on to the iPad?!

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