My outlook on spending is that I can't afford "cheap".
I feel this way for a few reasons,
1) Buying "cheap" usually means that I'm compromising on what I really want due to price/affordability. When I do this I usually wind up disappointed with the compromise and long for the item I actually wanted. The end result is that I end up buying the same item twice, which costs me more money in the long run than if I'd simply bought the item I actually wanted the first time around.
2) Buying "cheap" can (but not always) means inferior quality. In this case, if I buy something for half the cost but replace it twice as often an I really saving any money? In another example, is hot-rodding an inferior guitar really saving any money? Particularily once you factor in point number 1 above?
3) "Cheap" often doesn't hold resale value. Upgrading a $500 Epiphone with $250 worth of pickups and a few minor upgrades (nut, saddles, switch, pots, etc) won't give you the same return on your investment as buying a used Gibson Faded or Studio model and leaving them bone stock.
That said... "Cheap" doesn't have to be a negative, provided you do your research. Chances are you're not going to loose as much money on a Phase 90 as you will on an off-brand boutique phaser that no one has ever heard of. Plus there's a good chance that the Phase 90 sounds better anyway....
On the subject of name brands...
Unless it's a flavour of the week amp over on TGP most people won't give you $2000+ for your used $4000 off-brand boutique amp, however you can reasonably expect to get $1000+ for your $2000 Mesa head. I'm sure the rate of return is similar for pro quality Fender, Marshall and Peavey amps.
Buying a used Mesa head for $1000+ and selling it for $1000+1 makes good financial sense, particularly if you're not totally sure what kind of amp you're into.
Just because a European amp is shipped over to North America and sold at an inflated price doesn't mean it somehow became a better amp on the boat ride over.
That ended up more random and meandering than I intended... but I'm bored so whatever.