"Fixing large oopsies is just a prompt away" really depends on what you are doing.

I write software responsible for updating customer controlled devices. In theory, these devices may be in use for decades. I don't get to dictate when customers update their software. I have to use whatever software is on device as part of the update process, and the software update process really should work from every single version that's ever been deployed.

So whatever decisions I make / the team makes, generally we're stuck dealing with in some form for the device lifetime.