I doubt the idea behind using dynamic helpfiles has really been considered before, at the very least not in depth. I hate the idea personally, because I like the system as it is now, but this idea is both automated and not absolutely abhorrent, in my eyes.
Make it so if you type something like 'help dodge' you get information based on how much you know about dodging. Expert at dodging? You know it takes a bit of quickness and poise. Piss poor skills? Yup, you know that dodging a bullet IS THE SAME AS DODGING A WRENCH.
I have no idea the extent of power behind these helpfiles, but they can take into account your inventory, or what's at least hidden in your body as cyberware. I assume they could take into account knowledge of how to use a specific firearm you're holding. High pistol skill? Yep, that 2MM PopPop Tickler requires a high focus, some hand eye coordination, and a fuck load of luck to use.
Basically, as your knowledge of something grows, your ability to pick something up and figure out how much you know about it grows too. People can still share their RP experience.
I feel like this would need some level of stats to balance out with it too though. Otherwise people will just preload with a ton of skill to figure out how to min max a bit. It also requires that the helpfile program be able to determine things about your skills and stats, and also possibly on items in your current inventory. It works for chrome, doesn't mean it works for other things. For all I know 'help cyberware' isn't even a real helpfile, but a special command that does something unique. But I thought it was worth a thought and put it out for discussion.