I can only speak to US vehicles mostly. I know GM started using 3g cellular connections (that no longer work) somewhere around 2008 and later. For repair-ability and parts availability somewhere under 2010 I think is a good spot. You also get some of the newer safety features if that's on your list. But most cars in this era are heavily computerized, except for your more budget model stuff. 

Fully computerized engine management (throttle is fully electronic) electronic traction control with differentials and braking systems that are expensive when they break. 

90s into 00s is the newest without computers being too intrusive, but more likely to fail due to age, and parts are harder to find, especially computers. I have hoarded at least 1 spare electronic module for my truck for this reason, they are so hard to get PCM's for, and I usually have to program them because the correct ones are too hard to find.  

 gimme carberetors and alternators and fuck this digital shit

the whole edifice of complexity required to enable this tech is fragile, and it will be broken in the near future 

 This is very helpful, thank you! I wish there was a car sales website for gulag-free cars. 

That’d be rad 

 Tag me any time for stuff like this!

Step #1 care that your car spies on your whole life even when you aren't driving it
Step #2 should use an older vehicle that needs maintenance
Step #3 care that cars have become as disposable as tin cans and parts are hard to purchase on purpose
Step #4 Get past MFGs promoting disposable vehicles 
Step #5 understand that incentives only align with moving new vehicles and only ones that the MFG recommends because MFGs control what dealers can purchase by adjusting purchase prices
...

Most people haven't made it past step 1 yet. 

 Following up here. What are your thoughts on the 2008 Land Cruiser? I’m in the process of buying one now. Before I pull the trigger, I’d love to hear your thoughts. 

What’s the car’s gulag-rating 😂🌸🤙🏻 

 I owe you a response! I don't know really anything about Toyota's from that generation, especially Land Cruisers. That seems like it should be old enough to avoid the phone-home tracking systems. Likely new enough to still get parts for if needed. Take a look around at your favorite parts catalog website (Rock Auto here in states is good) and see if they have a good number of parts still available, ideally OEM from the manufacturer, aka "genuine parts" 

Also you may be able to use https://vehicleprivacyreport.com/ to see what it says. It might not have much from that era 

 What's the feasibility of removing the antenna and/or wireless chip in the car? Is there a hacker's website for different cars or anything? 

 I’ve found specific car models with instructions online - some in video form. Of course, asking a local mechanic if you need help is available.