I agree that DE should be a "Shall Issue" state, but this will never happen... and, if it does, it will carry a bunch of unpleasant baggage with it.
Last time Dover tried to make the state "shall issue" by simply removing the judges' discretion from the process, the bill was loaded down with so many anti-CCDW amendments -- required annual training, no carry in a bunch of really dumb places like doctors' offices, etc. -- that its sponsors and the NRA pulled support for it. The same kind of silly crap will happen again if such a bill gets introduced.
Besides, I hate to say this, but we have it pretty good right now. We fly mostly under the radar. We can carry in bars, schools, churches, polling places, and almost everywhere else. Big companies that put up "No Guns" signs in other states don't bother posting them in Delaware. (We love Costco, but the membership gets cancelled if they ever post such a sign). Also, such signs don't have force of law.
Publicity -- even the news coverage involved in reforming our "May Issue" system -- would ruin that. Imagine, for example, if any business could post a regulation-sized sign banning firearms and making it a crime to carry there. Thieves would simply hang out in parking lots, waiting for permit holders to turn around and walk back to their cars to leave their firearms... and then steal the guns and/or rob the clearly unarmed owners.
I can't say it's right to continue the awful discretionary permit process, but it may be less awful than the alternative.