itunes will not play songs from ipod playlist

Windows 8.1 user. I called in for support to Apple about 3 weeks ago on an unrelated issue.....since then I have had numerous issues with my itunes namely when my ipod is plugged into my laptop, I am unable to play the songs from my Ipod's playlist continually. I am unable to "check" songs in order to tell itunes which songs I want to play. I can switch to my my itunes downloaded music and check and uncheck songs just fine.......... I can play each song from my Ipod individually by going in and double clicking them but after that song has finished.............dead silence!

Does my question make sense and have I included enough pertinent info?

Thanks for any assistance.