#1
This old Fender Duo-Sonic came in the shop today, I instantly fell in love with it, but it's in really bad shape. It was originally white but the dummy who bought it stripped the paint and put on a really crappy finish with a shovel or something. Anyway, I asked him if he wanted to sell it and he said he would for 2000 dollars. Yes you read that correctly. I politely declined and went back to my buisness. He then went to the front off the store and proceeded to play a cheep Dean through a cheap amp (badly), he came to the back of the shop and told me he would give me the guitar if I bought him the amp and Dean plus 300 dollars on top of that, I could get the amp and guitar from the owner for wholesale price which is around 400 dollars, but I turned him down. Now I can't stop thinking about the guitar, did I blow it? I had a picture, but it won't let me upload it.
#2
This depends on a lot of variables.

A beat to hell and poorly refinished DuoSonic isn't worth $2K no matter what year it's from, though, so it's not like you lost the deal of the century here even if it was a vintage piece. At worst, you passed up paying $700 for what is maybe a $1200 guitar, at best you avoided being screwed by a beater from 1996. A really clean DuoSonic in a custom color from 57 is worth roughly 2500. A refinished one even from that same year is going to go for less than 1300, and usually less unless it's in great shape besides the paint. I've seen ones with the original paint going for 1200 just because they were roughed up a bit. If it's got a crappy refinish, you might be closer to 8-900, maybe less if it's had the hardware and electronics molested. I've never seen a price on a refinished DuoSonic tbh.

You have to host your picture on imageshack or photobucket or some similar service first, then paste the link URL they give you here.

So, no, I would not call this a missed opportunity. Maybe the pictures will tell a different story but this just sounds like a guy who knows full well he can't unload his crappy old guitar and is just trying to wheedle a new guitar and a bit of gas money out of it. Leading with the $2000 offer was just to get you thinking about big numbers and a crazy deal, and it sounds like you're still doubting yourself even though you did the right thing. Remember this the next time you go to buy a used car
#3
Hehe, yeah, I guess I just always loved Duo Sonics and thought 700 seemed like a decent price, now that I think about it though, you're probably right it wasn't worth the money. I'll probably just wait around a bit till I can afford an old jazzmaster (or build one).