I used to work for Lotus, supporting 1-2-3.

Mucking around with autoexec.bat, config.sys, emm386 etc to get 1-2-3 to load was fun. Lots of TSRs using up memory. The amount of times I had to tell people to create a "clean config" by commenting out most of autoexec.bat...

We also had to post people floppy disks with the correct printer driver on. No downloads in those days.

"What would a piece of software have to do today to make you cheer and applaud upon seeing a demo?"

I was at LotusSphere when Lotus Notes 4 was announced and demo-ed. That got a standing ovation.