Hi Ranger, every guitar you own teaches you something. It's not guarranteed that an expensive instrument will sound good and there are some great sounding mid-range guitars out there.
First off let's discount any instrument that is expensive because of cosmetics. Inlays and veneers are nice but icing on the cake.
Now we get down to sound. As you buy guitars you may be reacting to your previous main player. So say your last guitar was a bit over bright the next purchase might be woody and boxy. It's not just overcompensation but your ear and musical taste evolving.
There's also a big difference between a guitar you might use for recording or playing in your home and the kind of instrument you could gig or even get out at the family barbecue. Expensive instruments can remain in the case because you don't dare scratch them!
Martin and Taylor are big names and you do pay a premium. Checkout Freshman, BlueRidge and Tanglewood's mid to upper mid offerings for real tone value. Having said this a Martin or Taylor will always retain some resale/part exchage value when less well regarded names may not be accepted by stores, depends if you'll be trading in ever.
Beware guitar shop salesmen playing a guitar at you. Those guys are often way talented players and can make any instrument sound good straight out the box. My local store guy demonstrated a Yamaha jazz box to me, he could make it sing, I could hardly raise any volume from it. Make sure you play the guitar yourself and don't tell yourself 'it must be my ears I'll buy it anyway'. I played some astonishingly expensive Freshman guitars in a downtown store where the salesman read snippets from reviews that praised them to the sky, but to me they sounded overly trebley. Maybe my ears and fingers aren't ready for them yet...