I don't think it is a matter of like/dislike computers, but rather, as you mention, a matter of being able to diagnose and fix ones own equipment. I personally picked my 1999/2000 New Holland 675E due to the fact that it is peaty much all mechanical. No dealer only software to worry about. Another reason for going older is the emission equipment on the newer machines that we have all herd the horror stories about, especially the after treatment systems.
The machine I own is on my property, and is only used to maintain my property. The region I am in has very rocky terrain. My property has trees that are probably no larger than 18" in diameter as an average. I have had my machine for ~5 years at this point, and wouldn't trade it for anything. I like that it has the power to remove any stump I need gone (not as fast as a large excavator mind you), as well as the ability to carry a good load of dirt.
The front loader has moved some really big rocks over the years, and the backhoe has proven its worth as well. On the backhoe, I added an Amulet mechanical thumb. It could be a pain in the butt if you are trenching, but it all aces if one is wanting to grab a tree in order to hold, cut up, or move it, which is most of the work I do.
As far a a recommendation, I have an excavator (Bobcat E85) in addition to the backhoe. The bobcat is great for moving a lot of dirt fast, but slow going from point A to point B, and I mostly do not try to move a lot of dirt fast, and when I do, I still use the backhoe to move the dirt that I have dug. So, I do fully recommend a backhoe for property maintenance. As far as what year and brand, I would say pre computerized. What year that is differs by manufacturer. As far as brand, I tent to think the brand that has a dealer presence near by is what I lean towards. I am not stuck on New Holland, however despite some of the New Holland parts problems, I feel it is a great machine. My employer once has had many Case units in the fleet, and they were good machines as well. I have herd that JCB is a bear to get parts for, but a decent machine. Have herd Komatsu backhoes are a stand clear machine as well (I have no actual exp with JCB or Komatsu).