$350 is the deal of a lifetime for that car. G Body prices are getting higher every year. I only gave $500 for my '86 TBI Monte a couple of years ago and I don't think I've seen another running, driving Monte Carlo for under $1500 since. Mine is kinda rough but from your description it sounds like yours is in excellent condition. I don't blame you one bit for wanting to fix the car and keep driving it. Don't let your brother, dad or anyone else talk you into selling it if you don't want to. I'd love to see some pics of the car.
Now, to address the fuel delivery problem, my Monte Carlo just quit running one day as well. No warnings, it had been running fine and then it just sputtered and died. Luckily I was in my parents driveway at the time so I didn't have to have it towed anywhere. My problem was a dead fuel pump. I replaced it and haven't had any problems with it since. Your situation sounds similar to mine except that you said you can hear your pump running. I couldn't hear mine and the car would start if I poured gas into the throttle body so I dropped the tank and replaced the pump. I didn't really do a thorough diagnostic on it. In my case the replacement pump was free and the tank is pretty easy to drop so I took a chance on it. I'm assuming you'll have to buy any replacement parts you'll need so in your case you'll want to make sure to diagnose the problem correctly to keep from wasting money on parts you don't need.
I agree with some of the other guys that putting a fuel pressure gauge on the car would be a good place to start. You'll have to put a Schrader valve in your fuel line to have a place to test the pressure. Some guys go to the junk yard and get a piece of fuel line with the Schrader valve on it from another car and graft it into the line. I think there is a "kit" you can buy that is basically the same thing but I don't know exactly how much they cost.
The suggestions from the other guys are all possible culprits. Clogged sock in the tank, clogged/defective fuel filter, hole in fuel line, weak pump, restriction in the fuel line. All of those are possible reasons for the problem you described. I think that it's probably the pump going bad. It's getting weaker and not pumping enough fuel. Or, maybe for whatever reason you're not getting a full 12 volts to the pump. I've heard a lot of guys on here talking about finding rust and junk in the tanks after sitting for a long time and that clogging things up. While that's possible, I wouldn't think of that at first because you've driven so many miles recently. 1500 miles is several tanks of gas and it seems to me like if rust in the tank was the problem it would have quit on you a lot sooner. That's just my thoughts on it though. If you want to check for rust, dropping the tank is easy and free. It couldn't hurt.
Let us know how things are going. You've found the best forum on the internet and there are a lot of people on here who will help you out. If you lived closer I'd come over and help you check it out. There are several guys like that on here. Good luck and keep us posted.
