Yup - had the ability (and even tried last downturn) to buy but was consistantly outbid by overseas (and domestic) cash, after 10+ years of trying I finally decided to buy land and go through all the red-tape and expense of buiding something new. Turning houses into financial instruments was a real mistake.
Yeah, they won because they made things easy imho. Lower barrier to entry === higher user base. I would contest your 'everyone and their uncle had a site' comment, though - for flash you still had to be 'in the know' or curious of how the flash games/animations were made, and then be inquisitve and resourceful enough to get yourself a 'copy' of your preferred flash ide, then figure out how to package/host/etc. Sites like livejournal/tumblr are more akin to what you are describing imo.
Yeah I acknowledge modern web is superior to flash in another comment, but argue the accessability has gone down. Also I was not 'growing up with it,' I was getting paid to write actionscript, then as3, then as3 inside of adobe flex/eclipse.
Yeah there is a bit of nostalgia for me, admittedly. Modern canvas with a decent lib can produce flash-like/flash-superior content but the tooling is aimed at engineers while flash was aimed at creatives/general public (imho), hence why we got so much trash (accessability) but also why we got so much incredible stuff (again, accessability)
I'll let you know when it's all done lol - it's a long and expensive process!