I do prefere to upgrade a few components at the same time. For the past year I've had a bunch upgrades with analogue end, speakers and an amplification. Usually I do not pay too much of my attention on wires and buy them for the minimal match first.
What is your upgrade philosophy?
With at least 4 or 5 (perhaps as many as 7) components (plus cables) comprising the system at any given time, certainly one is the best at what it does and one is the worst, and the others in between. When you have the fever and spare cash, do you prefer to take the one weak link and vault it to the top of the pile, or would you for the same money upgrade perhaps 2 components to middling status? Seems the former yields a better system long term, but the latter would provide more immediate improvement. Is there a method to your madness?