Riley,
If I were to register my car as a classic over here I would only need to have it inspected once. During that one inspection they check the VIN and confirm that the paperwork is correct and they do a basic inspection to make sure the car is safe to drive on public roads. The registration is then issued with no expiration date and no further inspections are required. A classic car doesn't have to conform to local regulations but it has to be safe. This means that it can have red blinkers, no rear fog light, US style horrible sealed beam headlights and so on, but it has to have a safe suspension, steering and braking system. No smog check is done on classic cars.
The problem with that is that once the car is registered as a classic there are some rules that you have to follow - limited number of miles driven in a year, can't drive it to work, can't do any modifications to the car, can't cross any borders unless you get a permit. Not for me, I use my car as a car and I do make some improvements. So, I'd rather have my car inspected every year to be sure that it is running correctly and that it is safe.
If you know that your car wouldn't pass, why don't you make it right? I wouldn't feel right driving a car that I know isn't right. They made those rules to make sure that we are all safe out there on the road and not to make our lives more difficult.
This is what my car currently looks like:
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It was meant to pass... I made sure it does... with my own hands