Aside from the philosophy discussion...
Not that this is definitive, but the 550s VERY OFTEN leak from the "pucks" -- the cylinder head sealing rubbers, of which there are 6. A leak at the pucks will look exactly like the photo you've got there. These can be replaced by removing the breather cover and cam cover. You don't even have to pull the cam out, and you don't have to pull the head off, so you save all that headache. It's a 1-hour job if you know what you're doing, probably an afternoon if you don't and you're careful. Use a very small amount of Threebond or Yamabond (NOT RTV!!!!!!) on the pucks, and you'll never have to worry about them leaking again. The only thing you have to really beware of is making sure the lifters are pulled back all the way with rubber bands or wire ties before putting the valve cover back on. There's a good post in the FAQ detailing the process. It might be worth getting that far in and checking it out, before you get elbow deep in the thing.
The other common top end leaks are:
- The rocker shaft plugs and covers, on either side of the valve cover. This doesn't look like the leak you have, but I suppose it could be. In this case, you'll notice a weeping drip coming from the bottom of those covers, the ones secured with a single large Philips head screw. If it's caused by rocker shaft wear (early 550s were susceptible, later ones less so) you'll need a new valve cover to fix it. You can tell by looking for "ovalling" of the rocker shaft bore. Otherwise there are four O-rings which when replaced should do the trick.
- The head gasket right at the oil passageways, located on the far left and right sides of the head gasket. There are a couple of small O-rings there that keep oil from that high-pressure oil passage from leaking into the head gasket, and sometimes they shrink and fail. You need to do a proper top-end job to fix this leak.
I don't think weeping head gasket leaks are that common on 550s, but I could be wrong. The pucks appear to be the culprit far more often.