We have had several issues with our data updating. After talking to other municipalities it seems to be a huge flaw in the software for customers not to have the ability to choose an automatic nightly update. ESRI appears to have fixed the issue where you download a dataset it will create a new cache of data, however it could go days, weeks, months, maybe years before someone downloads that dataset again. There really needs to be a way customers can set their sites to initiate a nightly update of their dataset caches ....