The 550 is in fact a wet sump (oil inside the engine casing as opposed to the 750 which has an oil tank), and the dipstick is on the right-hand side of the engine...and remember to put the bike up on the centerstand when you check the oil level.
The oil pressure sending unit is mounted on top of the oil pump, behind the left engine casing cover. I attached a pic and it's circled as #1. You can pull this casing cover off without fear of anything pouring out (use an impact driver) - it's just a cover over the oil pump & front sprocket. Check the wire for a short, or maybe the sending unit is shot. They pop up on e-bay, just look for them. And while the cover is off, look at the shifter oil seal (circled as #2) because they are notorious for leaking. It's pretty easy to change these out if yours is dripping oil there.
Assuming the oil level is OK, it may be a short, it may be a bad sending unit, or the pressure may not be sufficient. Try pulling off a couple of tappet covers to see if the oil is making it up to the top of the engine. If so, you can probably sleep at night. If it seems dry up there, you may want to look at the pump.