No experience with your boat, but I replaced the shaft on my O’Day 322.
the shaft is inline with the rudder, but I:
1) removed the prop
2) removed the coupling
3) removed the stuffing box
4) pressed put the cutlass bearing
And that gave me (just) enough wiggle room to slide the shaft past the rudder. Took some paint off the rudder, but shaft came out. Same tricks to get the new shaft back in.
With a little luck and ingenuity, hopefully you can yours out!
Greg