How about:
California
New Jersey
Hawaii
Although Illinois isn't great, Chicago, FOID cards etc.
Massechusets has all sorts of funky permits too, but getting a CCW isn't exactly impossible there either, so that balances things out just a tad.
New York, ouside NYC, isn't actually too bad, but I think you need some kind of handgun permit and waiting period etc. "May Issue" CCW isn't too bad in rural counties though.
WI is great except for the lack of CCW, hopefully to be rectified soon, and that big city chiefs and sherrifs probably won't sign ATF MG, Silencer, and Short Barreled paperwork.
WI is notable as CCW is forbidden for everybody except sworn LEO's. We don't even have "May Issue" permits for the political and wealthy eliete, stalking victims (even if the sherrif is sympathetic) Private Eye's, Jewlers etc.
So on one hand, WI is currently just about the "toughest" CCW state, but on the other, it's good as it means all those retired LEO's, PI's. Jewlers, rich folks may have been on our side throughout the fight.
I stay in WI, because:
1. Other than CCW, the gun laws are really no worse than the federal ones/just about as good as any other place you might name. For a state east of the Mississippi, and north of Kentucky, we've got a pretty decent "gun culture" IMO.
2. Since I'm a law-abiding and relatively clean-cut guy, I have very minimal police contact, so I feel I could "get away" with CCW if I "absolutely had to", either on moral 2nd Ammendment grounds, or practical grounds such as being stalked.
3. We're hopefully a week away from getting CCW here.