At least in the UK, the increase in the contactless limit is accompanied by an increase in the frequency at which you're asked to confirm your card using chip+pin.
However, most merchants now have terminals that accept contactless mobile payments without a limit -- Tesco were one of the last to upgrade. So if you pay with your phone then you're back at risk of forgetting your pin.
I'd quite like it if there were some mechanism for setting device spend limits, as my smartwatch will do payments but with only a pattern for security it doesn't matter that I'd be happy only using it for sub-£5 payments: it'll quite happily authorise much more.
While on our first pandemic vacation about three months back I had to acquire local currency and briefly froze in front of the ATM as it'd been over a year and a half since I'd entered that PIN anywhere. I had to mentally cycle through a few I've used over the years until I remembered the current one.