Yes. Boat needs to be jacked up or backed pretty far off the trailer to clear. Be careful how you jack it. I'd use two jacks. You will scare the shit out of yourself if it falls off the jack. Don't ask me (or my floor jack) how I know this.
Once out, use TitanTNs "rebuild" thread. It's got part numbers for the grease seals and o-rings from NAPA. You'll want to make sure you get some 5200 (or similar) sealant to reattach the rudder port to the hull. It may be difficult to break free but with some heat and determination, you'll get there.
Also -- I considered leaving the rudder port in the boat. Glad I didn't. It would have taken twice as long. I'd remove it and take that right up to NAPA (when you think they might be slow.) They'll be able to get you all the snap rings and o-rings that you need to finish the job.
Let us know if you need help!
Former owner of a 1987 Supra Saltare. Current owner of a Malibu 23LSV.