I believe we will win, but it will be a difficult fight.
Scenarios (note that none of these is a final endpoint; time keeps moving on and things will change and repeat):
1. An Emerson-like case makes it to the Supreme Court and they declare the 2nd Amendment means what it was plainly written to say.
1A. #1, but the SC allows for some limitations that must be narrowly limited, mostly covering items that are demonstrably not useful for militia purposes (whatever such items might be). Comparable to current state of free speech.
1B. #1, but the SC on a higher degree of militia connection. Say, you'd be allowed an M16, but not allowed to bring it into highly localized venues like courtroom, sporting events, or the boss' office.
1C. #1B, but with the added caveat that you're expected to train periodically. DCM (now CMP) program kicks into high gear, with monthly semi-obligitory attendance and real training on automatics.
2. #1B passes, and the Loon-In-Chief declares that everyone will be assigned (and limited to) a Thompson Contender and must show up for training once a month. Miss your training, an you're deemed uninterested/unworthy and must go thru red tape to reacquire your single-shot Contender.
3. Boiled frog: as we're doing now. Gun ownership remains legal, but gets shamed and hassled into non-existance. A very slow process where we go quietly into the night...with a few people going nuts and being made bad examples of.
4. Prohibition, Part II: Banned Steel. NYC-like bans are declared (you still have the "right" in theory but not in fact). Things get bad, and the gov't relents.
5. The worst case happens, and the 2nd takes care of itself.