You can probably find the pivot pin on ebay, here in the USA there is a company on ebay by the name of NLA Marine that sells a lot of freshwater used outdrive parts.
Yes for sure grease the pin, with marine grease.
Just another tip, I coat the threads of all bolts/fittings for the outdrive, with Evinrude gasket sealer, or Permatex Aviation sealer, it seals the threads from water getting in and causing corrosion and that makes taking things apart, much easier.
Looking at your boat I can see how it'd be harder to get the drive on due to the Four Winns extended running surface design with the "sponsons" on each side of the transom mount. Might be good for handling but tougher to get in there. That makes getting or fabbing up a rolling jack even more important to make it easier. Using the strap like you have it, there is no way really to keep the drive straight and level, which is what makes it a 15 min job a 2-day ordeal, lol. When we get older my thought is we have just so many years when we can still do this, why do it the hard way? If I do it the easier way I can enjoy doing it a lot longer.
I too used to lift weights in my youth, now I do calisthenics instead of weight lifting, to preserve what joints I have left, lol.
As teenagers we did crazy things, that probably caused later orthopedic problems:
Bench pressing 270 lbs
Dead lift 300 lbs
Clean and jerk, 185 lbs
ah the foolishness of youth and peer pressure...