Why I design for my mom
startupsforupstarts.com
startupsforupstarts.com
However on actually reading the post :-) I realised I was unfair, since in this case your mum stands in for an active middle-aged internet user who is not a geek, but reasonably sophisticated. So, uh, carry on.
To make amends, I'll throw in some advice:
People who think middle-aged women somehow can't handle complexity are generally mistaken - look up some coupon sites, these women are explaining strategies that make your head hurt. So don't think it is necessarily a question of avoiding complexity when dealing with that population. In my opinion the big driver in that demographic is utility. You have to get to the point where it is obvious what your product can do for them as quickly as possible. They will take the complexity, if they believe it is necessary, but they don't want to waste their time.
[Edit: Forgot to say, obviously never base all your feedback on one person, no matter how typical you think they are.]
I also like to try to guide wherever possible. Even the most advanced users will appreciate extra guidance, be it tooltips, choice of words, or just the overall layout.
And yes, of course feedback shouldn't be based on a single person. That's my fault for implying it should. My point was simply that most developers design for themselves, and releasing yourself from that mindset is a good thing to do. That said, agile and metrics-based development is really the way to go. Get your MVP out there fast and iterate quickly.
The funny thing is that I knew she was doing notary stuff on the side for a long time now. I simply didn't realize she was using spreadsheets to manage it all.
The UI is really clunky still but most of that is a casualty of releasing something "ghetto, but useful" ASAP. I'm in the process of rebuilding it right now and it'll have a much prettier/useful interface rolled out in the next 3 weeks or so (though, mom's account is running the latest version of the UI). :)