This is reply to the question if anybody has had any recent experience in importing a car into Portugal and "is it worth it?". In short, importing a car form the US into Portugal is probably only worth it if you are prepared to go through hell to have that very car and no other car will do. The explanations and reasonings can go on for pages. The topic is complex, but very good and helpful information can be found here: https://impostosobreveiculos.info/
Here is our story
1. We imported a 1982 Land Rover from the UK to the Azores in September of 2020 while the UK was still "treated" as a EU member and were happy to pay $3,000 shipping cost because we were told (by Portuguese Customs officials for as long as we meet the requirements in 2. below) we could import the car tax-free.
2. We had to prove that a) the owner had owned the car for a minimum of 6 months prior to importation (the bill of sale is sufficient proof), b) the vehicle's owner had resided in the UK for a minimum of 12 months (this could be phone bills, utility bills, receipts from grocery stores, etc.).
3. Then we had to go through a long process of what the Portuguese "DMV" (department of motor vehicles) calls "homologation". In essence this is similar to a car registration. However, in the US (and in the UK) the car's registration states only the year, make and model of the car and color, I believe. In Portugal, the "registration" lists a hundred things including the type and size of engine, the tire size, etc. Let's call this document the "car's booklet". This booklet can be relatively easy to create if the Portuguese DMV database has all the technical specifications for the particular vehicle you are trying to import. But if they don't have all of the technical information in their database, then issuing the booklet can take a long time (4 weeks in our case) and can cost you some money (150 Euros in our case).
4. Once this document was finally created, the car had to pass inspection. Note that he inspectors will look at the Portuguese car's booklet and will check everything that is on it including, of course, emissions and performance of everything related to safe operation including brakes, tire condition, etc.
5. We failed the first inspection instantly because the vehicle had mismatched tires (not allowed in Portugal), which on top of that were not the type and size specified in the car's booklet.
6. New tires for a vintage Land Rover are not readily available on a small island in the middle of the Atlantic ocean. It took a month. And then off to inspection again equipped with brand new all-matching OEM tires. Failed again. This time it was an oil leak (so minor we had never noticed it) and wrong headlights (vehicles in the UK, apparently, have different headlight lenses and therefore different light pattern because they are driven on the "wrong" side of the road.
7. Eventually, the car passed inspection and was finally qualified for importation. But at that time (February 2021) Brexit was real, the UK was not a EU country any longer and the Portuguese Customs officials presented us with a 15,000+ Euros import tax and gave us a choice: 1. Pay the tax 2. Abandon the vehicle to the Portuguese State or 3. Ship it back (which is what we did).