Well, I solved this and I didn't. For anyone who is having a similar issue, hope this helps.

I created a new Module, and just put some crap code in there. Installed it, set up a job scheduler, and voila, the DateTime for Next Job started to work as expected.

Unfortunately, I have no idea what is wrong with that other module, however it was something module based. After I copied all of the business logic/code from the old to the new, everything still worked. So the module was tanked somehow (namespace or something weird that was crashing prior to next date getting set maybe). Don't have the time to find the problem, but I found a way to work around it.