I actually did start over from scratch in 2003.
1) How would you identify your allowable budget versus time? Time is irrelevant, it is the journey that makes it worth it to me. Budget, I never let stereo funds take away from the essentials.
2) Would you buy all used, all new, or a mix (including source material, audio input devices, amplifiers/processors, speakers including subs if any, cables, room treatment devices, architectural updates)? What would you buy used and what new? Used where ever possible. I picked up my KM-6 speakers (KG5.5) on ebay for $300-400. They where like new. My Marantz 2230 also off ebay last year for $129, completely rebuilt. Pioneer PD-M453 CD player new in the box for $10 at Goodwill.
3) What would you be trying to achieve - i.e., as close to a realistic performance as you could afford, or "something that sounds good to play stuff that you used to listen to when you were young". Probably the latter, it is about enjoying the music, so what ever sounds good.
4) How much would you be willing to pay for visual attractiveness instead of performance (% cost of the component)? This includes tubes and non-audio devices. Not much, function over form first. If it looks good too, bonus.
5) How much would you buy-and-sell in order to achieve your ideal system goal(s)? Would you try to minimize this? Would you buy without first hearing the equipment? What components would that be? I have always sold the old to get new. This has always been a rule of mine. I usually dont listen first anymore but I do massive amounts of research so I know what I should be getting.
6) How would you go about listening to the equipment before buying? If possible listen to the actual piece from the seller. If not there then locate someone near by that has the same model and listen to theirs if possible.