I'm asking for a family member who's in his 60s. He wants something intuitive that can handle the janky remote access third party program that he uses for work. Price isn't really an issue for him.

Ease of use is more dependent on the operating system than the computer itself. Is this a troll question? If he knows how to use a computer than he can use any computer.

If he's remoting in he doesn't even need something good because the comp he's remoting into will be doing all the processing.

Then any Dell laptop should be fine. My dad wanted one for the same thing and he's had his for 6 or 7 years now. It is starting to crap out nowadays but still.

Get a Windows 7 or 10 [64-bit OS] laptop [brand really doesn't matter] with an AMD processor and as much RAM as possible. Set it up with an object dock so that things are easily accessible from the desktop, then teach the person how to use it. My uncle refurbishes computers and sells them for cheap. Say the word and I can hook you up.

Tablets for Writing
 

Are there no tablets with built-in onscreen keyboards? Everything I read about says "buy keyboard separately". Surely there's one that allows you to write as you would on a mobile/cellphone, no?

As in a touchscreen keyboard? I would think that most every tablet would have that functionality.

That's what I would have thought. Maybe when they say "buy kb separately" they mean if you want a physical keyboard? See I never used a tablet before but am thinking of getting one. Do you know if they do have those touchscreen keyboards? Do you use a tablet?

Most have onscreen keyboards. The external keyboard is for those that don't like the touchscreen.

Yes, they mean a physical keyboard so that people don't think that it's built into the device. Is there a particular one that you're looking at? Because they're pretty close to phones and it would be pretty surprising to find out that one doesn't have any type of keyboard at all.