If I were in your position, I'd unbolt the post completely and put a straight edge across the top of the hull frame to confirm that there was any crush. If there is, same repair process as the deck, though make sure to grind away any broken old laminate. Do both at the same time, using the...
I would focus on the bottom of the post, looking for it crushing into the forward bunk area. If it looks solid, you're good. The boats are well made with respect to alignment and generally they're all the same with the exception of the mold changes after boat #130 give or take.
I wouldn't sweat it too much. One or two times from now, you'll be a pro. The mast is pretty light and if the path along the deck is clear, it's easy enough to walk up by yourself if the uppers are pinned on and there's somebody pulling on the tack line. It is nice to have somebody kneeling by...
By the way, do you know the spin halyard/bowsprit mast raising trick? To save time, I'll spell it out a little.
Tie the spinnaker halylard to the tack line securely. Make sure that the knot is about 10' up from the block at the end of the bowsprit. Extend the bowsprit all the way out. Cleat...
I'm trying to think what my mast step looks like but it's not something that I paid much attention to. My boat is also under two covers and some snow I imagine so I can't go look for you. I think that you have a little deck crush and need to repair it or fill it before putting on the new one as...