I recently upgraded my operating system to Windows ME and am very happy with the results. This was in conjunction with a hardware upgrade as well (to a Celeron 700), but I have had many fewer problems that I did with my prior Windows 95 configuration. Zero lockups of the operating system, for instance.

The best reference books I've found on Windows are the ones published by IDG Books, authored by Livingston and Straub. They are called "Windows Secrets" and they have an amazing amount of user information. Since Microsoft gives you basically no user guide other than the on-line help, I think a printed third-part manual is essential. I bought the one for Windows ME, and will give my copy of the one for Windows 95 to anyone who is a Windows-95 user and wants to pay the shipping (about $5 book rate).

This is a huge book with over 1100 pages and was published in 1997 at $50 retail. It has a CD included with lots of useful utility programs and some commercial programs you can try out for free. Let me know if you'd like it.