For the most part, driving around Disney isn't that difficult and shouldn't be a big problem at night. Of course, that's easy for me to say not being the one leery of driving after dark (I completely understand your concerns, though). Getting to most of the resorts for an ADR should not be an issue, even at night. Just like getting back to the All Stars should not be an issue after you're done dinner. Signing at Disney is pretty good. Make sure you know which 'area' the destination resort is in (Epcot resort, Magic Kingdom resort, etc). That will make things easier with the signs. The only place I would not recommend driving at night if you're uncomfortable, would be Disney Springs. That place can get a little crazy with parking and crowds.
If you have any experience (or are willing to try) Uber or Lyft, it can be an inexpensive alternative to letting someone else do the driving. Disney buses can work, too, but it will require 2 forms of Disney transport to get you from your resort to another - not always the most convenient.