I own four guitars:

The Epi and the acoustic I purchased from MF (both on clearance). The Gibson was purchased for me by my smoking hot and very thoughtful wife while I was at Airborne School. The MIM Strat, I purchased from the local Music&Arts after playing it for a while. It was on clearance for $260 plus tax.

For me, a lot of it comes down to price, or more precisely, value. That's how smaller stores compete with larger retailers: by adding value to the retailed product.

One thing I've noticed, however, is that when purchasing something $1000 or more, I pay more attention to how much sales tax I'm paying. A site like Sweetwater: not tax and free shipping: that's hard to compete with with the state of NC is gouging me for another 8% on top of my purchase price.

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Guitars:
Gibson Les Paul Special Faded
Fender Standard Strat
Epiphone LP-100

Amps:
Epiphone Valve Jr
Line 6 Pocket Pod
Pignose 7-100

Effects:
RP-1000
TS9 Tubescreamer
BBE Freq Boost

There are a few. Alpha Music in VA Beach is the only one I go to, but they have lots of vintage stuff WAY out of my price range. I go to them mostly for tech support. And to badger them about Fender Custom Shop $@!& that I will likely never buy.

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There are a couple here that I really like. One, Chambers Music, is the local Fender dealer. Lots of inventory, competitive pricing, nice people. Try out anything you want, very few punk kids to deal with.

The other is Johnny Guitars, which is my hangout. They mostly have used and vintage stuff but all in good shape. They know what I like and sometimes put stuff away that they think I might like. And they have a full stage setup in the store where you can plug and play anything you like, jam - bring a drummer, whatever you like.

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Ignorance IS bliss - and I am the happiest person here!

Metro Chicago has gobs of everything, praise be.