[Wlug] Shifting partitions?

A fast question: Anyone have experience with the stability of and general wisdom of shifting the Linux partition on a hard drive on a dual boot machine? I am trying to upgrade to a newer kernel and am presented with not enough memory on the Linux side of the drive. Encountered error message: <<An error occurred. Tour system has not enough space left for installation or upgrade (366821583>188726600)>> If the endeavor is too risky I can sacrifice the current Linux install, wipe the partition and install from scratch. (That does undermine the whole benefit of purchasing the proprietary upgrade package though.) Thanks. Colin