Ok, here’s how you fix it:

Just saying there are new requirements would be unfair to poor people that both a car before the new regulation. They would have to spend extra money now to fix something they are not responsible for.

Saying that car manufacturers have to fix all their cars would be unfair because they were selling car that complied with all regulations. This would not stand in court.

That’s why there’s no quick fix. Doing it fairly will be complicated and it will cost money. It’s easier for politicians to ignore the issue.

during annual checks

Most of north america doesn’t do that. Some place require a safety check to initiate insurance, after that most just wait for things to break or get pulled over by a cop/ministry of transportation.

Im also a little iffy about #2. We already subsidize drivers enough, making them pay for their lights or at least partly pay sounds reasonable.

I think a middle ground solution would be add the regulations for new cars and enforce the regulation when a noncompliant car changes owners. This way buyers of used cars should be able to research if that cost is likely to impact their model or not. It doesn’t take all the headlights off the road at once but it starts phasing out the problematic cars.