I have a 14-15 i would like to fix up and I have a few question the manual hasn’t answered for me.

The ledger plates are all dull so I am replacing the guards. I just bought one guard at TSC and put it on to insure it was the right type and i noticed it appeared to point down 3/4 inch lower than all the rest. Holding a piece of steel to it i found the the new one was parallel to the bar and all the rest were tipped up. Maybe that is why it has stacks of shims under the wear plates and hold downs. Are the guards supposed to be parallel with the cutter bar?

On the inside most part of the cutter bar, where slides in and out of the inner shoe it appears there should be a ledger plate. I don’t see one in the manual.

On the outer shoe there is a one sided ledger plate, I haven’t been able to find one like that for sale, does it come with the ledger plate kit from new holland?

I can't help you much but...
Some years ago I bought a 14-15 real cheap. It had all brand new guards on it.
I had thought about restoring it but then found a Ford 501 mower. I found that the Dearborn and Ford mowers both used the same guards so I swapped all the new ones over to the 501. Then sold the Dearborn for parts. (for a 12 pack I might add)
The end ledger plate was available from New Holland and I replaced it.
I'm wondering if the guards you bought from TSC are the correct ones?
I had the 501 manual at the time and it said to pound all the guards up or down with a big hammer to get them to the correct height. They did move easily when I did that.
Hth