Spend the most money on the speakers, only if you are serious about upgrading the electronics later. Speakers make the biggest difference in your system. The differences between dynamic cone driver, dynamic cone driver with ribbon tweeter, planer and electrostatic speakers are bigger than anything electronic. Of course, you have to buy the speakers that match your room and taste.
The GIGO argument is weak because a $500 or less (used) cd player does not put out garbage and is in fact closer than you think to the megabuck cd players. The GIGO argument was valid when it came to turntables and cartridges back in the '80s and computers. Not today with cd players.
Furthermore, Speakers are the not that easy to upgrade because they can be difficult to ship. Most people I know rarely buy used "big" speakers on Audiogon. Electronics are generally easier to ship, so experimenting is more convenient.