It's funny because it really departs from the typical "you're not their friend, players are your enemy and you should make life as difficult as possible for them and always be using random tables" vibe I get from most OSR stuff
Kevin Crawford just seems really amazingly on-the-ball about this. The first product I really saw from him was Black Streams, which was a system you could use to "buff" a single PC from an OSR/old-school game so they could solo an adventure if you didn't have the time/desire to get a whole group together. And in that he noted that if you really wanted, you could have two or more PCs like this and whilst it would be overpowered, it would be it's own kind of fun. And he's done a lot of these OSR-ish games at very different power levels, from "easily stabbed peasant" to almost Exalted-ish.
I think to even think like that you already have to have broken out of the mindlessly adversarial approach a lot of early OSR stuff specified. And it's notable that the resolution systems he's designed expect a good-faith approach from both players and DM, rather than an adversarial or competitive one.
WWN is particularly nice because the full edition essentially does what D&D 5E kind of threatened to do but ultimately didn't, and provides real tools for modulating the kind of campaign you want - especially with the further tools in Atlas. With both books you can go from utterly meatgrinder low/no magic play to PCs literally starting as Legates and Heroic characters, where they're more on part with again almost an Exalted character (albeit a Dragonblooded rather than a Solar), and a wide variety of settings in-between.
On top of that he's shown a real talent for solving longstanding D&D issues, a lot of which D&D and D&D-likes/relatives don't even tend to acknowledge - the stand-out one for me is what WWN calls "Execution Attacks", which are one-hit from-stealth kills or KOs, and implemented in a way that's both balanced and achieves the objective of getting that into the game.
(I will say WWN does sometimes share a flaw with D&D 5E that not ever modular system is super-clearly called out, there are a couple that - as with 5E - are inside the text of paragraphs - it seems like the nice call-out textboxes of the '90s are almost a forgotten art!)