Hello,

<<...There was a ton of metal shavings...-snip-...including several
metal chunks the size of a pinhead. What does this tell me?  >>>

A gray paste is OK on the drain plug magnet as thats pretty much
normal wear and tear on the internals.  Shavings and chunkage is
a good indicator that something substantial is/has failing/failed.

<<.. I know the Bentley says it should be 9/16" below the filler
(how the heck does one measure that??), but does this equate to
a liter? Could this lower oil level have contributed to more wear of
my tranny?  >>

Your guess is as good as mine here.  It was common practice
at the last dealership where I worked to drain the gearoil per
VW TSB's and then refill with a portable  'oil boy' and use the dial
indicator to judge how much we were putting in.  Or, if the gearoil
began to come out the fill hole then it was called good.  I wouldn't
think that being slightly low, I bet it was more like 1/3-1/2 of a liter
down, would contribute to excessive wear in the low miles you've
put on the vehicle.

<<..rolling at ~5mph, clutch in, there was clicking as I slid from
N to 1st, but not the other gears....>>

Sticky or worn synchros do not usually manifest themselves as a
clicking noise.  Rather, it becomes difficult to engage gears and/or
you get some grinding going in.  Clicking noises are associated
with CV joints and the fact that you hear it clutch in or out at low
speeds then I'd think that that is where the problem lies.

Then again, my wife tells me that thinking isn't my strong point!

-Todd Hill
 VolksWerks Transaxles
 Olympia, WA
 360-412-0948