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I suggest the Honda Civiv LX - It's under $19K MSRP and it is sold in Europe.
One thing to keep in mind is that the warranty will not be valid in Europe and you may have a hard time getting some lighting, body, or emission components as the standards are different there. Also, they may not be able to perform any safety recalls as well as they may not apply to Euro models.
But standard maintenance parts should not be an issue.
One thing I missed - you may have to homologate the vehicle - essentially make it conform to EU specs regarding lighting and emission standards.
Certified (CPO) Golf (Hatch or Wagon) or Jetta Sportswagen TDI...
I agree, but would caveat with a 4-door GTI!
But I don't know if the CPO coverage would transfer from here to there?
I've not been to Portugal, but if it's like the other countries / cities I've been to on that side of the pond, roads can get pretty narrow pretty quickly. Paris, London, Munich, Amsterdam, Switzerland, etc. (Yeah, I did the tour bus trip...)
Since you're limited as to what you can do once you bring the car there, i.e., once every ten years, you would really have to find a car that's well worth the sticker price here and a profit there not only to pay for shipping and ownership costs, but also for the replacement vehicle. Making $30k profit, for example, on a Mustang may sound great, but when you have to pay that $30k for a replacement, you're just breaking even, especially when you don't get the same style and performance in the replacement.
You could always go with a reliable and safe choice, Mercedes. An E-Class sedan, diesel if you can find it, wouldn't be a bad option, though you may not stand out with a unique vehicle. I'd also consider a vintage SL, since you're in Portugal, assuming that you're not driving too much and don't need an especially practical vehicle, i.e., four-five seats and cargo room.
A Volvo C70 hard top convertible or an S60 can also be had for under $20k, but no diesel option, and Volvo is pretty common on the continent. You may also find an XC70 if you need a wagon in Portugal.
The nice thing about the Fusion is that you can get a hybrid version which is very quiet and smooth and returns good fuel economy.
You could also likely find a Lexus ES hybrid for your preferred price point, which uses standard Toyota. For around $20k, you could find a 2013-2015 ESh with lower mileage.
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All the world's a stage, and all the men and women merely players: they have their exits and their entrances; and one man in his time plays many parts, his acts being seven ages.
~William Shakespeare (As You Like It Act II, Scene VII)
As you have probably already figured out, the purpose of the law is not to open an avenue for an immigrant to make a quick killing by skirting the provision. It is to offer an immigrant the convenience of bringing along his own car as household effects. If it were that easy to use this as a cash cow, there would be plenty of advice out there on how to do it.
OP, if you are a bit mechanically inclined, let me suggest a BMW E30 325i, or 318i. Simple old cars, easy to work on, European in origin so probably not hard to find parts or service. And the 325i cars at least are going up in value. I would go with a 5-speed, not AT.
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