I am an oldtimer. It comes with the saggy jowls, bald head and seniors discount. Most of the rifles I hunt with are older than I am, but not all. I like stainless steel and I like modern optics. If you are going to shoot bear, at any distance, scopes with a custom turret make sense. As I said before, black bears are the most undefined animal I have ever hunted, and it's not just because of their shaggy coat and even colour. Small bears look like big bears, especially at a distance. I have been fooled and shot hundred pound bears thinking they were three hundred pound bears. Real trophy bears stand out. The wide head, small ears and sway back let you know when you are in the presence of a special bear, but all the others are just a carbon copy of each other. If you are doing the holdover thing it makes a difference whether it is a small bear or a big bear and, unless you have some reference point to indicate the size, it is very difficult to tell. If you can hold dead on at every distance it helps.
Two more points: In deep, lush vegetation, which is what they like to hang out in during the spring months, little cubs can disappear. I almost shot a big bear once that wouldn't run away from me until I saw the deep grass moving a few feet from her and realized there were cubs handy. When I saw that I backed away and she seemed visibly relieved. If it wasn't for that grass moving I wouldn't even have figured out she was a female because she was quite large. Another point is bears are one of the easiest animals to stalk. When they have their head down feeding you can get closer, sometimes much closer, and that is a real thrill - that is real hunting in my mind and it feels like it - but I live in a world with lots of bears so I can be fussy.