Pantz,
First, good job on tackling this beast and all your battles on your own. Keep up the good fight. I had a mixed bag of issues when I bought my used boat, and have always managed to get through without the shop. As always, best of luck.
On my boat the first time I removed the outdrive it wouldn't budge because the drive shaft and motor were not properly aligned. I can also note that I always spray the OMC gasket glue on the gasket when it is mounted, so there is some resistance there, but that glue is not very strong.
On my first attempt my outdrive was so stuck from being out of alignment with the motor that it flat out would not budge by human hands. So, I reconnected the trim hydraulics and used the trim up to push outward on the drive and tapped the sides with a rubber mallet until it worked loose. Then I could pull it off by hand.
Now, I use the hydraulics every time to help guide out the drive. The hydraulics help hold the drive steady so I can work alone. Works great for me, but of coarse it is properly aligned now (and properly greased), so I only have to push out with the hydraulics enough to break the gasket glue.
I'll be removing my drive and replacing the Sierra u-joint bellows at the end of the month as I just found a 1/8th inch crack in my u-joint bellows. Cleaned it an repaired is short term with high flex RTV until the end of boating season. So I'm sure everything will be coated in surface rust again. (never ends....never ends)
BruceB58 noted to use an OEM u-joint bellows........I fully agree as this Sierra boot cracked after only two seasons of use (season here is February through October).
I'll be going back to the OEM bellows also, they seem to be thicker to me. To be fair to the Sierra bellows, I haven't had a change to look very close for pinch points or if something rubbed a hole in it. (my first u-joint bellows had a hole from the grease zirc shooting out through the boot)
Keep up the fight.
Offrddrver