Thanks for the pics...Helps alot.
HandyGuys, please check out picture #5 especially....
Looks like that jamb was prepped for qlon (kerf style) weatherstripping, doesn't it?
If so, you could go to a door shop or lumber yard (probably not a box store)
and buy 3 pieces of that product. Pemko and some other companies make it.
It installs into that kerf like these pictures:
Remove the existing weatherstripping and install the qlon.
Make sure the latch is holding door tight against it.
This won't solve the aesthetic problem of the uneven reveal
but it might help keep you warm this winter!
An added benefit is that it won't stick to your paint the way
your current weatherstrip does.
Does that make any sense for your situation?
The Door Guy