The 8300 will definitely feed letter size cut sheet. I do it all the time. The 8300 does need a rather hefty trailing edge margin of about an inch, but if the target image size is too big, it would just clip the image. However, It should print.
I'm on a Mac, so I can't say for PCs, but I think the problem might be related to the page setup menu which on the Mac may need to be accessed from the System Preferences Print and Scan dialogue box. Anyway, check to see that under the page size choice in the menu and actually in a submenu when you click on "letter-size" that you have the "letter size (cut sheet)" option picked. If there's another one of the other letter-size choices selected there it will force the roll condition situation you are encountering.