One thing I liked about MacWrite and MacPaint was their simplicity. They didn't try to do everything. Same with MacDraw (the first object- or vector- based drawing tool). I still hunger for the simplicity of MacDraw. Also of WriteNow, which (as I recall) was written in machine, or something, which made it very very fast. Also hard to update.
Same with MultiPlan, which became (or was replaced by) Excel. I loved the early Excel. It was so simple and easy to use. The current Excel is beyond daunting.
Not sure what Quicken begat, besides Quickbooks, but it was also amazingly fast for its time, and dead simple. Same with MacInTax. I actually loved doing my taxes with MacInTax.
And, of course, ThinkTank and MORE. I don't know what the connection between MORE and the other presentation programs of the time were. Persuasion and PowerPoint both could make what MORE called "bullet charts" from outlines, but neither seemed to know what outlining was. Word, IMHO, trashed outlining by making it almost impossible to use, or to figure out. Still that way, too.
One thing to study is cruft. How is it that wanting software to do everything defeats the simple purpose of doing any one thing well? That's a huge lesson, and one still un-learned, on the whole.
Think about what happened to Bump. Here was a nice simple way to exchange contact information. Worked like a charm. Then they crufted it up and people stopped using it. But was the lesson learned?
Remember the early Volkswagen ads, which were models of simplicity, like the car itself? They completely changed advertising "creative" for generations. Somewhere in there, somebody in the ad biz did a cartoon, multi-panel, showing how to "improve" those simple VW ads. Panel after panel, copy was added: benefits, sale prices, locations and numbers, call-outs... The end result was just another ugly ad, full of crap. Kind of like every commercial website today. Compare those with what TBL wrote HTML to do.
One current victim of cruftism is Apple, at least in software and services. iTunes is fubar. iCloud is beyond confusing, and is yet another domain namespace (it succeeds .mac and .me, which both still work, confusingly). And Apple hasn't fixed namespace issues for users, or made it easy to search through prior purchases. Keynote is okay, but I still prefer PowerPoint, because -- get this: it's still relatively simple. Ugly, but simple.
Crufism in Web services, as in personal software, shows up when creators of "solutions" start thinking your actual volition is a problem. They think they can know you better than you know yourself, and that they can "deliver" you an "experience" better than you can make for yourself. Imagine what it would be like to stee a car if it was always guessing at where you want to go instead of obeying your actual commands? Or if the steering wheel tugged you toward every McDonalds you passed because McDonalds is an advertiser and the car's algorithm-obeying driver thought it knew you were hungry and had a bias for fast food -- whether you have it or not. That's the crufty "service" world we're in now, and we're in it because we're just consumers of it, and not respected as producers.
The early tool-makers knew we were producers. That's what they made those tools for. That's been forgotten too.