I think you hit the nail on the head: the leadership of the NDP is terrified of being called socialists. A lot of them are Rae-era veterans and remember very clearly the utter ratfucking they took from the establishment, and they're desperately trying to appear "sensible" to appeal to our gatekeepers.

The problem is that they'll always be called socialists, no matter how much they try to appease the Very Serious People that run things. Floyd Laughren has a tale about this, where he & Rae met with the banks and larger businesses of Ontario with their fully-costed plans for the next four years, only to have the banks say "That's nice, but we're still going to destroy you". Mulcair went right of Trudeau in 2015 and they were still calling him a radical left Marxist socialists. Hell, they call Trudeau a radical leftists despite his being more right-wing, economically, than Mulroney.

Meanwhile, Conservatives can be as fundamentally unserious as they want, and are never held to account.

The NDP needs to stop ducking punches, stand up, and make the wealthy explain why giving them more tax cuts will somehow make things better. Co-opt the "Make ____ Great Again" slogan, but make it about marginal tax rates and being able to see a doctor same-day. And they should do it knowing that the wealthy will have a hissy fit.