People who are already behind the curve professionally, and who aren’t willing to grow will become all but useless in short order.
I would argue that in the long term it would be more of a drain than a benefit. In that case, it may be more economical to keep the current staff.
The exception to that is #3, where a shop may be staffed by PC-illiterate people. The bottom line is profit, and the means to this goal is by getting the best and most economical tools for the job. However if this is for profit, then cost is a major consideration. Others have budgets, or simply don’t want to waste money. Some people like to brag about how much they spend on this or that. If it’s just a hobby, then cost may or may not be an issue. If one stays within the bounds of the question, the next question that must be asked is whether this is for pleasure or commerce. That list really is more general than the question that it asks.