UPDATED TEXT (I wasn't allowed to edit it past 15 minutes, which is rather inconvenient):
Contact PT Embassy, they have all the forms to fill out to avoid import duty. They maybe let a large tractor in without duty because you would be doing agriculture which is welcomed or even supported by the local gov. My tractor was a medium garden lawn tractor.
If you can not search for properties yourself by coming here and spending time on Pico, you can hire someone to do that for you. I can do that for you, can drive extensively around and look for something that matches your criteria. While agent listings may be easy to find online, FSBO are not online and must be found by driving and even walking. That takes a lot of time, gasoline, taking photographs, emailing them etc. If it was close to my house within 5 or 10 km and a couple drives I would do it as a favour of course, but I live 40 km from East Coast and it's a long winding road to there and steep slopes up and down. If you don't have a budget for paying someone to do that you can try to find someone on the East Coast who would be willing to find you the local FSBO properties. I know some local properties FSBO where I live, but I am not familiar with Piedade etc. although as I mentioned I can drive there and get it all looked up. If you want me to do that send me your search criteria etc. all in the detail. Yet those properties may be gone 2 years down the road.
If I am on the East Coast (where I go to rarely) I will try to remember to take my camera with me and take photos of some of the VENDE SE FSBO properties if I find any.
Oh and you may find it useful, the locals work for around 500€ per month but more skilled office etc. is about 800€ per month. Hourly pay for unskilled is 5-6€ and for skilled is not much more is 8 to 10€ per hour.
Before I moved to Pico I got some of this info that I am providing you with, but in a wrapped-up tinseled and romanticized form. In a form like they told me you get milk delivered to your door every morning (it is not), free this and that, free wine, free veggies, well, part of that is true, neighbours give me lemons and oranges sometimes and I got a bottle of wine as well and gave them stuff as well and there's a fresh fish truck driving around on a speaker as well, well you got to pay for the fish of course. I did not move here to get the free stuff anyways. I had my house cleverly advertised by the previous owners with the ruined parts cleverly omitted
so when I came here I saw the ruined parts but I still decided I wanted it and now it is restored by me, in a traditional fashion. Send me photos of your house and I will send you mine, in a private msg.
I am giving you raw unaltered info, no frosting or romantization.
Before I moved to Pico I was placing ads online and I was asking the locals in search of crew, plumber, roofers, advise. All I could find was an electrician. No one wanted to do the roof, plumbing etc. Those who did theirs skills really suck. So thanks to someone from another island and another country who gave me a lot of great advise and contacts I had guys from other island in the Azores. Right now I know 2 carpenters on the island but they usually very busy. I can have them do things if placed in a queue, perhaps a couple months in advance. I'm waiting myself to do things in my house.
They told me that bananas grow better on the south side of Pico. Not sure how much better. I am working the soil to plant my own bananas and i am on the north side, but it is the least steep slope here in the island and plenty of Sun anyway and thus most of population lives on the north and west side, such as Madalena, Bandeiras, São Roque, Ribeirinha, probably about 11000 on North coast and Madalena out of 15000 total pop.
Also, no waxing of vegetables in Pico supermarkets....
The vegs spoil fast though. I believe you can eat the peel of cucumbers safely.
You must not forget how you will immigrate to this beautiful country of natural beauty with family values and REAL houses that can withstand high wind, unlike Oklahoma cardboard boxes, or will you be spending 3 months a year at a time. Otherwise you can easily immigrate if you purchase 500 000 € worth of property (or invest) in Portugal. Contact PT Embassy, you may be able to find a helpful and patient person there or much better contact Regional Government of Azores, they are very helpful, just be patient, it takes time.
Talking of time, I am now 4 months into waiting for my PT Drivers License. They told me I may have to wait up to a year. They say it is normal. They are working on it very hard! I gave them photo of my own, cost me 5€ photo and 24€ for the DL. All you do is collect a bunch of docs and no need for road rules exam or even driving test, but you must learn European road signs and rules for your own safety. You will have to take a medical test though. It will cost you 2€ and a short conversation. They most likely will not measure your fever, your weight, nothing. Unless you look sick at the time of the driving medical exam. All you do is give them your USDL and a bunch of docs they require and they will take your USDL away (permanently, so say farewell to it before going to get PTDL) and give you a paper doc (A4 but a bit longer than in USA), a temporary DL without photo glued in (?), so DIY?? and then your waiting begins. Once you receive your new PT DL buy champagne and celebrate with friends. If you are alive by then. The wait is most likely worth it as you will be able to drive around the entire EU and beyond with it. Maybe even in the US.
I don't know your budget, but I may decide to sell mine, it is 5 acres and remodeled house with an apartment; the land is flat(ened), made in large terraces of about half acre each.
DO NOT even attempt to import a car into Portugal! Buy locally, just remember cars in PT are very expensive, even as used ones. Best is to buy from friends some used junk and repair it. I bought from a dealer for 9000€ same car that sellfor around 1500€ in UK. And it has a severe transmission problem. Long story... Don't buy from the car dealer next to COMPRE BEM supermarket. They did not repair that problem, but they used my car for their own driving and used up most of my gasoline in my tank, drove about 200-300 km on it. So, if you do IMPORT a US car into PT, please share your experience here. If you get away paying very low import duty or even none, we would be very interested to know how you did (get away with) it.