Facing $1500 in repairs to get the $1000 clunker through inspection is the main driver behind the improper use of Historic tags..I'd bet my lunch money on that. Heck, it cost me over $500 to get my parent's well-maintained and clean-looking 2000 Grand Cherokee through MD inspection. It had always passed VA inspection easily every year.
It was part of that for me.
The truck had 190,000 miles on it and the trans was slipping in and out of overdrive. I had recently rebuilt motor laying around the shop so I decided to drop the $1,000 to rebuilt the trans in a truck worth $1,500. Unfortunately, emissions caught up to me before I could finish the project. The day before my emissions was due I went to the MVA, got historic tags. Few weeks later I dropped the new motor and trans in at the same time.
It's a bone stock 95 S-10 (now with less than 400 miles on the motor and 30 miles on the trans) and I have no problem paying less for it just because it's 20+ years old. I drive it like 3 miles every couple of weeks and I followed the law.