I did a bunch of work to the car a couple months ago. Replaced the head gasket, rebuilt the carb, replaced the distributor, and a whole mess of other little projects along the way. After all this work the car ran great, but I started to notice a pretty serious oil leak a couple weeks ago. I tried several times to find the leak, but never could so I just kept filling it up when it got low because I was busy and didn't have time to do a full diagnosis. I never noticed any problems and figured I would just keep doing that until I got a chance to look at it.
Unfortunately, I decided to push it the other day while driving on the freeway. The oil light came on, and I drove another 15 miles or so to my exit before putting more oil in. When I got off the freeway, I noticed the car was making quite a bit of noise, but I hoped it would go away with some oil. While most of the noise went away, I noticed there was still a rattling/grinding noise in certain gears, at certain RPMs. I drove it a little more and the noise only got worse. Mostly showing up in the 1500-1800 RPM range. I decided to drive to Arlington (about an hour drive) because my friend has a shop and it's close to the PicknPull.
But I never made it. After a few minutes of driving I could tell the car was doing much worse. Eventually the car was rattling very loudly in every gear, but was completely silent when I put it in neutral. I messed with it a little bit by shifting back and forth between neutral and 5th to compare sounds. It sounded perfect in neutral, but was ridiculously loud in 5th. Eventually I felt/heard something get stuck and it felt like something broke. I didn't see anything fall off or anything, but there was a definite clunking noise (like that of a loose part) coming from the middle of the car. At this point the car died and I was able to coast up the off ramp and into a gas station. When I tried to start it there was basically no response (just a slight click) and we immediately called a tow truck.
The car now sits in my friend's shop and we're starting to work on it, but I have no idea where to start. I took out the started just to see the flywheel and what not, but didn't find much out. The gears on the starter are a little worn down, but nothing crazy. And it looks like it retracted appropriately. The flywheel looks good as far as I can tell, but I have no idea what it's supposed to look like.
So that's the situation. If anyone has any ideas, please don't hesitate to chime in. I can use all the help I can get. And besides, I know there must be a few of you out there who enjoy these types of mechanical puzzles.

Thanks in advance!