Tools get upgraded as the tools our tools use evolve. PHP has evolved, and so SilverStripe has developed to accommodate new features and better ways of doing things. It makes sense there's going to be big changes from time to time that take a lot of effort to accommodate but yield good rewards.
Magento 1.x to 2.x was a significant jump.
It is possible that we might move to strict typing in SS5 - mayyyybe. That might be a little annoying.
But we won't do that without releasing an upgrade tool to assist
I'm hoping the upgrade between ss4 to ss5 will be more straight forward than from ss3 to ss4. Strict typing should make the upgrade from ss5 to ss6 more straight forward I'd imaging. Forcing project code to meet an expected standard should make it more reliable through an upgrade, surely.
The primary pain point in upgrading from 3 to 4 was the namespacing. This should not be a problem again on a future upgrade
@firesphere that's good to hear
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