Not copying photos despite plenty of space

I find this frustrating.
From time to time as I update my iPhone, mostly having videos of comparable size swapped in and out, or Podcasts being updated, I'll get the following error message:
"Some photos were not copied to the iPhone... because there was not enough free space on the iPhone to hold your photos and albums."
However, there is always plenty of space shown in iTunes. For example, iTunes is presently giving me that error message while reporting there is 576 MB Free on the iPhone. In this case, it is not uploading a total of 300 photos.
What is strange is that the same set of photos were previously on the iPhone when I had as little as 300 or 250 MB of free space left.
What gives?
The only way I have gotten around this in the past was to do a hard reset and restore the entire iPhone: a lengthy and hopefully unnecessary process. However, it does suggest to me that there is room for everything: it just won't sync normally.

I got it to work and here is how.
In this case, most of the content is audio songs, 6.38 GB. One playlist alone is 6.19 GB. The single photo album to be synched to the iPhone is only 40 photos/77 MB.
Started with 202.7 MB free space on the iPhone. Again, sync at this point fails to add the photos.
1a) iTunes/Music tab: unchecked "Top Songs" playlist (6.19 GB)
1b) iTunes/Photos tab: unchecked "Top Photos" album (77 MB)
1c) Synched; success (tons of free space)
2a) Checked Photo album "Top Photos"
2b) Synched; success
3a) Checked Music playlist "Top Songs"
3b) Synched; success
Now iPhone space is as follows:
Capacity = 7.08 GB
Audio = 6.38 GB
Photos = 30.3 MB (apparently resized for optimization)
Apps = 241.2 MB
Other = 264.4 MB
Free = 176.7 MB
So in summary, remove enough audio to get the photos synched, then re-add the audio. No need to reduce the size of the audio; it seems songs fill remaining free space better than photos.

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