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There are adjustable chains on the mower deck that hang the deck to the mower that can be used to gain some height. Be careful if you are moving these because you could end up with an uneven cut. The bolts that hold the chains in place are mounted in slots, you can loosen the bolts and slide them in order to make adjustments.
Can you cut in the transport position? Normally not, the belt will not line up with the pulley system properly and you will have belt problems. If you don't have belt problems when in the transport position then I don't see a problem with mowing in that position. When checking height how are you doing it? You must measure to the blade tip in order to measure cutting height properly. The mower deck edge is not a good place to measure to because it may not be the same