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Niko,
I am assuming you want to cut some 4.5" holes for access to bolt the leaning post. You can tap the deck and find where the stringers are located, hopefully they are not where you want to cut.
As far as a jig saw, like you said, you may not have much room under the deck. You can shorten the blade a bit. Drill a small pilot hole and check the distance.
You could make a round jig and use a rotozip too. Thing is if there isn't enough space for the jigsaw blade there would not be room for your hand to bolt things up either. You'll probably have room I hope.
If you use a jigsaw you may want a variable speed to slow it down a bit. The glass will to dull the blade quickly compared to wood. Use a bladeon the finer side as not to chip out too much gelcote.
Do you have some kind of backing plate or block to spread out the load underneath? There will be allot of torque on that post when I am leaning on it!!
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