Kal-El:
Sounds like you're making good progress. I haven't been ignoring this thread, but I've been on the road for damn near the whole month of August. The cover hiding the shifter seal holds nothing but gunk, you can pop it off without having to dump oil or whatever, it just encloses the front sprocket, etc. No seals, just on & off. There's a thread somewhere when I changed my seal - good advice on getting it out in it. I agree the shifter seal - #2 in the pic - has nothing to do with the sending unit, but will make a mess under the cover & drip if it's shot. Once you know what to do, it's an easy change-out. I changed mine, and then found the oil pump cover leaks just a little too. I recall it's a funky sized seal, so I'm holding off for winter. The oil pressure switch sits on top of the pump - #1 in the pic - and monitors the pressure right at the pump, but unless it's a monster leak, I doubt it will really impact the switch. A clogged or shot switch will. I briefly looked into where an oil pressure gauge could be added to a 550, but there was no convenient spot for a permanent one so I gave up. To test the switch, or pump really, I recall there's a port on the "points" side of the engine that can be used, but would suck for a permanent installation. The idiot light is good to have, but good lubrication is the real deal, so if you have good pressure -check with gauge- and good distribution -check with jelly jars on top- then I'd be inclined to drive it while looking for a replacement sending unit.
...and I've been using Shell Rotella T dino oil.