At what point do you then slip on the timing belt and what if a groove/ridge do not line
up perfectly?
Start with finding the timing mark on the flywheel and have it by the pointer.
I'm assuming you have the 5MM 'A perfectly sized pin gauge'
Close may not be good.
Also there is a 'sucker hole' in the injector pump. The pin goes in but not fully.
This might be a good time to loosen the 3 bolts on the front of the pump.
Do NOT loosen the center nut.
'some gauge block gizmos locked the camshaft'
The real tool gets centered with feeler gauges the same size on each end.
The cam lobes for cylinder 1 must both be pointing up at this point.
At this point #1 cylinder is at top dead center, the cam is locked for #1 cylinder, and the injector pump should be locked for #1 cylinder.
If the 2 locks are in and the crank pointer is correct the timing should be good.
If you never did the belt on a TDI the sucker hold might be the problem. It got me once.
Try to rotate the pump be the 3 bolts back & forth while pushing the pin it.
If it goes in further the pump was not in time.
The cam pully should be loosened if you want to make sure it's on the money.
There's a few long threads on doing the belt here, one is a sticky.
Worth reading one of them a few times. A lot of detail and pictures in them.