The hope has always been if Maryland gets their portion of 404 widened, then hopefully Delaware will get really angry at the backups on their state line from 404 dropping from 4 to 2 lanes and actually do something about it.
If I were a betting man, I would say Delaware widens 404 from the coast to US 113 first because that is where more population growth is happening.
With Maryland, I just looked at the State Transportation Plan and the only thing on the plan related to 404 is a $450,000 study for the 404 corridor from Sennett Road (where road goes from 4 to 2 lanes currently) out to MD 16.
No actual construction will start until 2029 at the earliest and then it's a matter of having a Governor who is going to be friendly to the Eastern Shore when it comes to highway projects. Hogan was great, O'Malley was fair, but Glendening was horrible.