Each time you pick up the guitar it should be an enjoyable experience, if you are frustrated you are not practicing the right songs. You should never feel overwhelmed, and each time you are complete with your session you should have a high degree of satisfaction...

Does this sound like you? It sure wasn't me for a while, until I found a great teacher... here is what he told me.

That high degree of satisfaction can be can be achieved a few different ways:

the first is through dumb luck,
the second is through a quality instructor or advisor,
the third is discipline + a combination of understanding your skill level.

The good news is you don't have to pay for an advisor if you can find a site or program that walks you through the beginning steps to play the guitar. There are many excellent sites out there such as ultimate-guitar.com & guitarnoise.com

But back to the main point... (improving your skills)

In any sport or field you have your novices, intermediates, and experts or pros. The process to reach each any of those levels should be completely understood as you begin to learn ANY new skill that you decide you want to learn. In this case, we are talking about the guitar.

One of the first lessons you need to understand is that talent does not make you an excellent guitar player. For those that already understand this, I congratulate you, as it took me a few years to understand. I dismissed all excellent guitar players as pure talent and never stopped to think about the discipline it takes to get to the level that they were playing at. (stupid, I know)

For those that want to take their playing to the next level, here was my secret: Leverage the power of your mind to play your guitar when your driving, at school in class, or at work. Picture the fretboard, "see" your fingers playing it effortlessly.

One of my favorite things to do is to sit back in my chair, close my eyes, and climb up & down the A minor pentatonic, starting at the 3rd Fret E, to the 10th Fret high E ....

Despite what you think you do not need to pick up the guitar to practice, at the very least, use your mind instead...

I hope this has helped!
Can you say stream of conscious?
Yeah Dimebag is not the "Greatest Guitarist" of all time... Hendrix maybe... I must go get food to eat with my mouth

$250 for an amp? wow. is it worth it to invest that much in the amp?

Some valid points - you posted in the wrong section of the forum though
Schecter C-1 Classic (Antique Amber)
Ibanez JEM 7VWH
Crate Palamino Class A tube combo
Digitech RP80 Multieffects pedal
Ibanez TS9 DX Tube Screamer