I've put a lot of thought into it, and I have arrived at the conclusion that it would be impossible and impractical for me to think about a $2500 guitar right now. Maybe in ten years or so, if I'm actually making money by playing guitar I might get a guitar worth that much, but I just can't do it now. And I think that's a good choice, because I'm not bothered at all by it. And pretty much all of your posts confirm it's the right choice too.

My grandparents are rich enough that $1800 isn't a large enough drop in the bucket to hurt them. My parents aren't rich, otherwise we could probably work out an I pay half, you pay half sort of deal. The issue is more of that I don't even want to ask my grandparents. It just seems wrong. And I don't want to give up my weekends. And I don't want to be 16 and already be in debt $1800. In fact, I'm not even go to bring up guitars at all with them, usually they give me some cash on my birthday and I'll just add that to what I have saved.

The guitarist who owned the guitar is semi-famous, but not really. Yes, he inspired me to start playing but when I think about people like SRV, Clapton and Hendrix had more of a lasting impact. My tastes have changed.

Yes, the guitar would be worth $2500 if he hadn't played it and I know for a fact that he played it on tour. One of my friends is a very good friend of his, and she's the one who let me know the guitar had come up for sale.
The guitar was originally sold by him to raise money for charity, and he has about 35 other guitars so it's not like it was his main one or anything. In fact, it seemed like every time I saw him live he had another guitar with him.
Also, it's not a Fender. If it was a Fender I would literally be in tears.

And yes, I'm a player. I don't collect guitars, and I can be a little rough on them. That's sort of why I liked the idea of the road worns (and why I mainly use my Squier), I don't have to worry about it.
I gig much more than I used to. I've in Church quite a bit, on a weekly basis. That's really where I started, looking back on it. A couple of years ago I couldn't even sight read the chord chart and I'd get scared when I had to play the intro of a song alone.
Recently, with my band, I've been playing things like festivals and Church benefits. And they actually give me leads and let me make up my own riffs in some of the songs, which is something I could never do in Church.
Yesterday my band headlined a concert. We played for two or three hours, and it went real late.
I played my first set of music I like (60s rock and blues), at a festival a few weeks ago. That was the one where I had to play musical chairs with band members. It looks like summer may be a little dead though, since my band wants a break (who needs a break?) and the other bands that have invited me in haven't gotten back with me on practice times yet. The only bright spot is that I'm going on a week long trip to Austin for the first time specifically to play guitar and I should learn a lot. It's an expensive trip and I think I'm going to sell some of my gear so that I'll have some cash for it.

I have some things like a Digitech multi effects board from when I started that I don't need. Since I've gotten my Fender amp, I haven't touched my Peavey Classic 30, so that can go. It took a lot of effort to get that amp, and I was really excited when I got it, but I can't think of a practical use for it.
I have six electrics (although it looks like my brother wants his Squier Tele back, so I really have five). All but two were bought used, and all of them are "budget guitars". I like modifying them, most notably I have Texas Specials in my Squier Strat. It sounds better than any of my others, and it's a beater, so that's what I gig with. It's like having an ugly, rusty car that can out race all your friends because of the mods you've made.
My MIM Standard Fender is having trouble, it needs a new nut or a new bridge or a set up or something to keep it in tune. And my T-60 has a dead pickup that really needs to be replaced. But those are my only two major repair issues right now. Oh, and my drums were a free gift from my non-rich-side-of-the-family grandparents. My grandpa plays drums in a western swing band out in west Texas and he got them used. He upgraded to a better set. They aren't the best drums in the world, and they've seen quite a bit of action (well, that is if you can call western swing "action" ) but they work fine and I'm very thankful for them. If he hadn't given them to me, I probably wouldn't play drums and playing drums is something I like second only to guitar.

Thanks everyone for helping me to clear my head. I'm sorry if I've just been thinking out loud, but that's what I have to do sometimes. As far as the Custom Shop Fender thing goes, I'm just going to wait. Maybe sometime after college if I actually can make a living doing this.
I'm still going to sell off some gear that I don't need anymore and the money will be for spending/living expenses in Austin. What ever I have left, plus my birthday money, will be saved for a better Fender than what I have now. Whether that be a Road Worn or an American Non-Custom Shop Fender of some sort, we'll see.

And someone (maybe several people) here had another very good point about gear not being so important. I was thinking about that too. I know people who can make a stock Squier sound better than a guitar three times it's price and I want to do that more than I want an expensive guitar. If anything, my money would probably be better spent on some new blues CDs to learn from.


EDIT: Oh man, this is the longest thing I've ever written. Maybe I should turn it in at school.

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I think you made the right choice. Not too shabby for a 16 year old. Looking back, I made a lot of wrong choices back then.(Probably make the exact same decisions now though )

Sounds like oyu are getting into the deep end of the pool, as far as playing goes. That's awesome. best of luck!!

Remember you have a long time left in front of you to get expensive gear.So fill in the wait by playing your tail off, and get real good. Then you can justify any purchase to yourself as a reward!!!

I will always have a soft spot for my first guitar though. It wasn't too expensive, and I really favor my Strat (The first guitar I ever bought new, and really only one of 4 that weren't used,) but I still feel right at home with the oldie. it got a lot of miles on it, and I am glad I still have it.

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I'm not an expert, but I play one on the internet.

I think you made the right choice. Not too shabby for a 16 year old. Looking back, I made a lot of wrong choices back then.(Probably make the exact same decisions now though )

Sounds like oyu are getting into the deep end of the pool, as far as playing goes. That's awesome. best of luck!!

Remember you have a long time left in front of you to get expensive gear.So fill in the wait by playing your tail off, and get real good. Then you can justify any purchase to yourself as a reward!!!

I will always have a soft spot for my first guitar though. It wasn't too expensive, it was used,and I played it in bands for around 7 or 8 years before I got my Strat.I really favor my Strat (The first guitar I ever bought new, and really only one of 4 that weren't used,) but I still feel right at home with the oldie. it got a lot of miles on it, and I am glad I still have it.

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I'm not an expert, but I play one on the internet.