djwyld

We recently had this problem when building devices that don't have a physical keyboard (surface pro, tablet etc). Basically bitlocker doesn't think you will be able to enter a pin at startup so errors out. You can get around this by setting some reg keys in the TS to override the behavior, follow this URL for instructions: https://blog.basevision.ch/2014/07/deploy-tablets-like-surface-or-lenovo-helix-with-windows-8-1-and-bitlocker/

Yeah, you will want to upgrade to at least CU 3 as it includes the following: Software distribution and application management 3007095 Applications may not be downloaded in System Center 2012 R2 Configuration Manager

What version and CU of sccm are you using? There was an issue a few versions back where applications were unstable when running from a task sequence. Alternatively, you could create a package version that is used in the TS. Cheers, Dave