I would love to try that, but the biggest issues are: safety and hygiene. Having a good parking spot can be a challenge already in the US/Canada where parking lots are everywhere and urban infrastructures were designed around cars. You can crash into a trusted someone's backyard, but is that actually a van life then?
And hygiene. Not even getting into pandemics, you need to be really disciplined not to waste water and be close to somewhere you can actually shower without worry. Can't rely on sponge baths forever.
Waste disposal is another issue. For van-lifers its simply discarding the nasty bag, but for garbage disposal? Not to mention the homeless opening up garbage bags to rummage through.