I don't think that a few stops and starts with head pressure should be a big factor. As often as A/C units cycle on cars I doubt that pressure ever has much time to bleed off.
Exactly. A car's A/C uses an electric clutch, and it goes on and off
often and suddenly. I assume you will use such a compressor, too, as
you don't want to waste power running the compressor when not
needed.
The 3-pt cyl is always last in the series (or bypassed entirely) because
it's valve has no power beyond. The hoses you saw are between the
PB of the aux valve and the IN of the 3-pt cyl.
As for case drains in hyd motors, it is true that if your back pressure
on the OUT port is greater than 500psi, a case drain is called for. But
you will likely operate your 3-pt cyl for only a second or so, so you are
probably OK without one, IMO.