I have been exploring server-based apps online the last few months, trying to help an offline group with 100+ members develop a platform for sharing news and schedules. As with just about any volunteer entity, there is, to put it politely, a wide range of computer comfort among its members.
On one side there are the fast adapters who are quick to learn new things and find it fun to do so. In the middle, there are the semi-techs, or later bloomers, who may know the basics of a few favorite functions such as email and word processing, but not a whole lot more. On the other end of the spectrum are the semi-Luddites with high computer anxiety who mouse around reluctantly.
And the icing on this layer cake is that all of them use an assortment of software and CPUs, old and new.
In short, it's an IT management nightmare to get them all on the same page doing similar things online at a similar time. What seems like the simplest instructions aren't so simple at all for those who are flying blind and clicking by rote without much of a mental paradigm.
If they all stuck with their own applications and their old computing habits, supporting them all would become more than a full time job. That's tough for any entity run by volunteers for free.