Ok, I rewrote giving money to free characters. Now you can give any sum, and it checks against character's current gold. If the sum is way too small, it won't end well.
Also now you can ask for money, providing that disposition is high enough. They will give you a random sum based on their gold, but never more than 1000. And they won't give you anything if you are much richer.
All options use days flags, thus cannot be used every day.