As odd as it sounds, the biggest place the pro-gun side has won in the last 30 years has been at the federal level with legislation and courts. Assault weapons bans looked like a fait accompli after Britain, Australia, and even the state of California passed their own in the 80s and 90s - now they're becoming something of a political third rail. The Heller ruling made blanket bans like semi-autos or handguns near impossible, unless a similarly major Supreme Court case overturns it later. At the state level, CCW rights have only expanded as "packers" have proven to be remarkably responsible thus far.
I think the place we have to watch out for is with executive branch rulings made by an anti-gun administration, and with future state-level legislation. ATF rulings and executive orders usually lack the scope of legislation, but they can be created pretty much by fiat and are very difficult to overturn in courts. An anti-gun administration that knew what it was doing could put a couple of them in the right places and make life difficult for us.
And state-level gun control is easier to get passed than federal-level gun control, while economic factors are continuing to pack Americans into a smaller and smaller group of cities. Ironic how the telecom revolution was supposed to let us work from anywhere, and yet it centralized us more than 20th century manufacturing plants ever did... Anyway, by 2040, 70% of Americans will live in only 15 states. If most of those states have gun control, then half of America will lose their gun rights without a single federal law being passed. And that makes AWBs, ammo control and other fun legislation much easier in a generation, when it becomes less "let's ban ARs for everyone right now" and more "well, everyone else is already doing it..."
EOs - we can't do much about those other than vote in presidential elections. I think state laws need to be the battleground we stay looking at. Apologies for the political sidetrack but I think it's important to take stock of where we're at and where we're going.