

I think the biggest systemic issue in most places is that most people don’t actually know how to train people, including most senior staff. Very few people are actually natural trainers/instructors, so they have to be trained in how to train, and the expectations that they do so has to be part of company culture as well as time baked into the workday to do it, because it DOES take time. It pays off huge in the long run but it can be hard to see the forest through the trees if the management themselves don’t know or understand the value.
As much as I hate corporate jobs they’re generally better than small companies about having a formalized training program. It’s a shame because there’s so much garbage in corporate culture that a lot of small businesses don’t want to implement the good with the bad.
One thing I’ve seen over the years is that a TON of businesses have NO IDEA how to be functional. It’s a person that started in their garage and managed to grow and they just do stuff, and keep just doing stuff and hiring more people to do stuff and quickly outgrow the garage but don’t introduce sound business practices that you need to run things effectively. It’s crazy how many businesses are like that.
There can only be so many different server config combinations for algorithm, crypto mode, key size etc, so it would be trivial to have a bot try several combinations and nail your setup on the 5th try or whatever, especially if you selected “standard good” setups, which you should if you’re opening a port.
But overall it will weaken the protocol and there is a risk, even if it’s small, of a downgrade attack being discovered. Simply by having options means that it’s possible to trick the server or force it into a more vulnerable state. You can’t get rid of that except by completely removing the options in the first place because there will be literally nothing to downgrade to.
WG just isn’t into that risk. It’s cool if you want it and I won’t say you’re wrong in general because everyone has their preferences and makes trade-offs to set things up the way that they want, but in this particular context it goes against the design principles of WG by introducing complexity and risk, which is not what it’s about. There’s many other options if that’s what you’re looking for, and a lot of them are just as great/secure.