I tried to get regular Virginia inspection on my '75 K25. The first thing he did was look under the hood (visual emissions equipment inspection) and say "it doesn't look like it's all original", and one park light also looks like it has a crack, so it won't pass regular inspection. I think he gets plenty of business inspecting newer cars and didn't really want to take the time to inspect an old vehicle.
Most newer cars are disc brakes and they have an OBD port, so checking brakes and verifying other working equipment is a very quick job. On an old K25 with FF axle it would be really a PIA to inspect the rear brakes. They are fine and would pass, but inspection is a lot more work.
I settled on using Virginia Antique plates and it hasn't been any issue. You still need liability insurance, but antique vehicles don't need inspection or emissions, and there is no property tax. When you get the plates in VA you have to show that you have another vehicle to use for your DD, but that's about the only requirement. IIRC the mileage limit is supposed to be no more than 150 miles for parades, shows and other events, but I doubt they ever bother checking unless you do something stupid. I've been up and down I-66 and I-95 many times.
