As usual Denise is quite perceptive. That skeg might very well be in the way for cleanly inserting your new shaft.
If the skeg is a problem then at a minimum you might have to remove your engine's mounting bolts and scootch the engine forward 6" or more to insert the shaft from inside the engine room.
I just installed a new shaft on our Tartan 27' but there is not skeg so it was easy to access from outside the hull.
Good luck.
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