I normally am in the "leave it in" as most people change fluids too often in my experience. But in this case, I would change it. I "had" and drove a restored '66 230SL for ~4 years so some familiarity.*
WHY:
General things your concerned with in oil life - oxidative and thermal break-down, contamination, shearing out of grade. In your case you aren't likely to be getting anything but the first. But over 20 years, it can be substantial. The effect is more pronounced on dino oils vs. synthetic, also.
Both the boxes are vented so some air is always reacting to oxidize the fluid, as well as any condensation accumulated or not burned off. So the diff has suffered 20 years of degradation, too.
WHAT:
In the transmission, I think that was originally a Borg-Warner unit using Type A fluid. In which case, I'd look for a modern synthetic Dex III quivalent. It will meet the original specs and be backward compatible. It will also match the original viscosity, which DexVI will not. In my experience, this matters. Most current Dex/Merc or DexIII offerings are not synthetic, but pennzoil makes one that Pep Boys often has quite affordably. Whatever you get, make sure not to get any "LV" labeled stuff, that would be DexVI.
This one would be ideal, for example - synthetic for added stability, added seal conditioners for long-term storage:
https://www.pennzoil.com/en_us/prod...sLzIwMTZuZXdzbGV0dGVyLz9sb2NhbGU9ZW5fdXM
Redline and some other boutique makers also make full synthetic DexIII. If I paid more for one of those, I would then skip the ester oil additive (more below).
Diff: a synthetic 80w-90.
EXTRA:
Into each, I would add the spec'd amount of Lubegard additive, red in the tranny and yellow gear oil in the diff. Not so much for the aw additives, but for the ester oil content. It will coat the components for corrosion protection (like the sperm oil in some DexII), and condition the seals.
* - I didn't own the car, but a good friend did. He left it with us for several years while he was overseas. I could use it at my discretion in exchange for storing and maintaining it. So I did learn about maintaining this vintage MB, though I think by '66 they had in-house transmission vs what may be in your '59.