Here's my $.02 worth.
Don't know very much about the 982's, except they were made from 80-85, probably weigh a bit more, have 4 more HP, and go 3mph faster. I wouldn't question so much reliability as much as parts/implement availability. I'm sure some other members can address that.
I've owned several 2165's along with numerous other 2000 and 3000 series Cubs.
(and 5, 6, 7&7500 series!) I did like the 2165's I had, and gave one to my father-in-law that he likes and is going strong. I did have a minor common problem with 2 of them, the needle valve in the carb sticking, and personally prefer the v-twin Kohlers in the 2000 and 3000 series, but overall it was a fine tractor.
Question; was the engine rebuilt in the 982?
One part of your text caught my eye.....long steep driveway....steep lawn...with those in mind, and if fiscally possible, I would consider a 3000 series with differential rear lock. Makes a HUGE difference on steep terrain. Not to mention larger snowblower, PS, and hyd lift. And, they're still making them.
However, assuming you are only looking at the 2165/982, I'm partial to the newer Cubs, but it sounds like a hard call.
And one more mention of slopes, my father-in-law is making some (deer)trails behind his house up some very steep slopes, mowing the underbrush. I was quite impressed when I saw them....to the point I didn't believe the tractor could actually climb that slope. But, the rear tires are loaded on his 2165, I'm sure making a big difference.
Hope this helps, good luck!