Nate - congrats on your first trip around the block. Nothing like a vintage car, and a Y block powered one at that!

You will get there. I drove my 55 Fairlane with a 272 EVERY DAY in the early 90's when I was 16. Even in the snow! (yep, everybody is groaning right here). They are fine, powerful cars once tuned and in working order. Remember, this car has been sitting quite a while...just needs some TLC.
First things first -- SAFETY. Make sure those brakes are working right. If you can't get to every wheel, then by all means make sure that your front wheels have good working brakes. But, don't forget that the original master cylinder only had one line going out to all wheels...so if you have a leak at the rear, essentially you are affecting the operation at all wheels. Make sure there are no leaks, and adjust those shoes properly.
On the fuel issue (good point on using the starting fluid to see what you would get for combustion), is there any chance that you may have run out of fuel? Don't know how much you put in initially, but odds are after you put in that new tank you didn't fill it up with 17 gallons, right? How much have you been at idle, tuning the car, turning over the engine and pumping fuel, etc? I don't mean to sound stupid,,,, but this very thing happened to me one time. I thought it was a fuel pump, etc., but on a whim I went underneath the car and tapped the tank with a hammer...EMPTY! Arggghhhhh!
My fuel gauge was way off...
just a thought before you go checking everything else out.
Daniel JessupLancaster, California
aka "The Hot Rod Reverend" 
check out the 1955 Ford Fairlane build at www.hotrodreverend.com