Do photo filenames repeat themselves when taken on my phone

I have a situation where the photos are backed up on a time capsule. Photostream is on as well. When I select a photo I want to see it picks up another photo leaving me to believe the filenaming of the photo may repeat after 9999 photos. Can anyone confirm this? Also if I have 5 years of photos on my phone how do I selectively delete them in bulk if I only want to keep say 1 year on my phone but archive the rest.
Thanks

These pics are not of the sync process at  all.
As the manual explains, you import these as you would with any digital camera.
iPhone User Guide (For iOS 4.2 and 4.3 Software)
Copying personal photos and videos from iPhone, iPad, or iPod touch to your computer

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