1. bought a NES in 2008 after suddenly missing them really badly, and after suffering a through games with musical scores significantly worse than i had remembered, searched the internet for tools to make compatible soundtracks and found famitracker. at the end of the year i found 8bc (which was already in "only old 8bc was good/8bc was never good" mode). of course before that i had experienced composing MIDI music for doom wads, for years and years, but not everyone really thinks of that as chiptune, and i hadn't heard the term until a few years ago
2. good question. i do feel as though i make music in this style simply because i love famitracker, and if it made music for musicboxes or player pianos then i'd love that instead. but chip to me implies the need to cut corners and deal with very limited polyphony, to make the most out of a very limited range of sounds.
3. tim follin's soundtrack for solstice. you get a prog jam and a serious piece of dark background music with enough sensitivity to make up for the prog jam, haha... it shows that the best composers were already looking for ways to push the envelope.
4. dunno. you can make chipmusic in the latest version of cubase if you really wanna - it's just that the old grey boxes won't let you make anything BUT.
and ilkae i'd like to hear more about your frustrations with the topic