#1 - you are correct. The way I do it is to tee into the line and run the plastic line through the drivers side water drain, out behind the front left tire and then just bring it up through the open window. The MV gauge may just read vacuum and not + pressure so you may have to find a 0-15 psi gauge to use for this purpose. You will have to get on the steepest hill around (I have to drive pretty far to get to it around here) and then floor it going up the hill. Works best if you can find one on an interstate somewhere where you can get some speed up.

#2 - I would try to fill up with new fuel at the first opportunity and probably dump a bottle of some type of diesel additive in there.

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Jim