Greetings,
Mr. 01. Yup, seems you have a plan of attack. You may have to do all of the above BUT, once hauled, your "problem" may be obvious. I replaced a rear seal on a Velvet Drive transmission a while back while in the water. First time I ever did so but I had previous experience replacing oil seals before.
De-couple flanges, slide prop shaft aft, release (unbend) locking washer behind that humongous nut holding the flange to the transmission, undo nut, carefully pry out old seal, clean housing, install and seat new seal carefully (do not put it in backwards), replace flange, apply sealant before putting on nut, re-torque nut, bend over locking washer, slide prop shaft forward and re-attach. Done.
It will be of an advantage to partially drain fluid from the transmission so it won't gush out when you remove the flange/seal. Lots of diapers underneath potential leak points and some cold libations in the cooler to celebrate upon completion.