Honestly, the maintenance part is where most tools like this fall apart, but it doesn't even matter unless owners actually see value in what's captured. i've worked with dozens of business owners, and the real question is whether they ever go back to that portal. Are they pulling it up when they're hiring, training someone new, or handing off client work? Or does it just sit there as a nice one-time exercise that gets filed away?
And then on updates - is the system smart enough to pull changes from their daily stack, or does someone have to manually tell it something's changed? Both issues stack on each other. There's no point solving the update problem if the documentation isn't doing a job for them in the first place.
