Well its now a year since I was in the business, so things may have moved on, but Microsoft were offering cheep Windows 98 to charities, I think at £5 to £10 a pop. However it would seem sensible for them to move onto offering Windows 2000 instead. The charity that I worked for looked at this and there were just too many regulatory hoops to jump through for us to be involved (in practice it would mean a lot more work for me).
As for long term support, well people came back to us constantly for help and we found that a problem, we didn't have the resources to provide anything other than basic help and they they were told they were on their own. The Blackpool Computer Recycler project with its 1 week of computer tutorials seemed a good way of getting people "trained up" before letting them take a computer home with them. This was funded by an European Union grant for deprived areas. This paid the wages for the person to run the week long course. After that they were members of the Blackpool Linux Users Group and could get (to a degree) on going support from other members of the group.
I agree most computer users will not even check help files before asking for assistance. That is sometimes the fault of the help systems, that they assume too much prior knowledge or are written too technically, but this is not always the case. The reality is that most computer programs and all operating systems are big complex things and take a fair bit of learning. People (in general) just want to know enough to get what they want to done. Even my hardware students did not want to understand what they were doing when they partitioned a hard drive and formatted it, they just wanted to learn the required sequence of keys to press to do the job. Exercises when they partitioned a drive into more than one partition left them bewildered. They could never see the utility of doing this for Windows and because this was a requirement for Linux it rendered Linux in their eyes as obtuse and unnecessarily convoluted and thus of less utility than Windows.
After a while you become jaundiced to the human condition. This is one of the reasons I like this place. There is such a patience with people, like me, who has "stupid" questions and who need hand holding.