-> I am a little leary of XP simply because I know I will become the "support
-> contact person" on this family-members PC, and I am not very familiar
-> with it.  We use it at work, and it seems to work fine, but when something
-> goes wrong, it seems to me to be a lot more unforgiving than Win9x.

 That is what I have found. But like you I avoid halping people using
Win2000/XP. there is still a plentiful supply of people I can assist
that are sticking with their Win95/98 systems. 
In fact I still have 4 OEM copies of Win95OSR2 avaialble for installing
on machines for Senior Citizens that are willing to work a Name
Extraction program for a frined of mine..

By the way a couple of weeks ago I ran across a place selling Win95OSR2
licence and EUOL's only(NO CD) for $15  :-)  :-)
--- Platinum Xpress/Win/WINServer v3.0pr5