Hey OrangeLeopard, welcome!
When I came up (in the old school mentality) conditioning wasn't taught as being necessary, but, on the side my seniors definitely endorsed it. We didn't use the foam pads in those days, and in sparring or doing full speed techniques, shins would collide a lot, as well as bone on bone contact. I did "toughen up" my shins, which helped quite a bit as well as in a few street encounters, where the shins collided, they fell down bleeding and welting up, unable to stand effectively, and me not even feeling the strike, not even bruising afterward, and still standing. Even today, while at work I started striking a hard building support column in the hall. I always remembered those old days, when I was told to toughen up, whenever possible, sitting in class etc.. because you might be in a fight, swing and miss, hit a wall, or the top of their head and break your knuckles.
To sum up, I would say it's up to your situation. If you get into a lot of encounters due to your occupation (bouncer etc..), or where you live, or whatever, Toughen up, at least to some extent, It's good to be as prepared as possible. I would start striking a hard surface, lightly at first, from a short distance, maybe an inch or two, and only a few times, with each side, each day. Slowly build up power, and distance of the strike, until eventually you can fire a full strike, at least once.
If you don't need to do it, don't worry about. I don't think it's done much any more in most schools, unless breaking is a necessity (boards, bricks,etc..)
