So, as you guys know, I have been fighting with the brake system on my 55 Wagon. It has not been fun, however it gave me a chance to clean up a lot of the road grime and crud at the wheels.
Since I had to replace some of the brake lines and replace the master cylinder, the system was pretty much empty, so I used a vacuum brake bleeder, and it worked okay, but not great.
So I got my wife to do some pedal pumping for me so I could get a good bleed on the brakes. We went back and forth, at all four wheels for at least 45 minuets, yelling back and forth
"you pumping?"
"yeah"
"got some pressure?"
"yeah, I think so"

and each time, I got little to no fluid (or seemingly air) out of the bleeder valves. Again, I tried all 4 wheels and was pretty discouraged as I know I had gotten some success with the vacuum bleeder.
It was getting time to leave for an appointment so we called it quits, but I hopped in real quick to see what was up as she had said the pedal went all the way to the floor most pumps.
I pump up the pedal and show my wife "you pumped it fast-ish like this to build pressure?"
And she looked me right in the eyes and said "Nope, I apparently was pumping the clutch" my beautiful loving wife, who took 2 years of auto mec in high school, who owned and drove a manual transmission vehicle for the first 10 years I knew her, was pumping the clutch to help me bleed my brakes

Now onto my problem (which you might see coming) after about 35 miles of driving (getting gas one day and groceries the next) I drove to work last night and just as I was getting there, shifting became difficult, and it would go hard into gear (aftermarket overdrive included), and then when trying to back into my parking spot I ground the hell out of the gears going to reverse.
I added some gear oil to the transmission this morning before leaving in hopes that it was the issue, since the clutch pedal felt normal (and I'm due for a fluids change soon anyway) but it didn't take too much, about .25 quarts, and it didn't fix the issue.
In the 20 minute drive home, it got worse. I limped it home, but now the clutch pedal goes at least half way or more to the floor without any resistance and pretty much doesn't engage (or just barely/not near enough)

I haven't had time to climb under and see if it is something simple, and of course I assume the worst. So I'll ask on here, what things should I look at first, before I have to take the whole thing apart (which I am not sure I am qualified to do)

Thanks all

VTWilly