Uhhh...
Yeah, I have a thought... stay in your lane. That is, if this story is even real, which I doubt (or at least parts of it are fabricated or embellished).
It just doesn't make sense to me.
First, you're a ramp agent. You're not typed in a 737, nor are you an A&P. You actually have no idea what you're doing or how to do it.
You, as a GA pilot, were going to do a real walkaround of a 737? Do you know what a "real walkaround" entails. Do you know that when you get typed on an aircraft, you have to do walkaround training. And every 18 months, you have to do walkaround training as part of your periodic checkride?
In the Air Force, we pilots were made to pass a "Aircraft Servicing" class annually just in case we had to divert to a base without maintenance and had to check and service the oil, or hydraulics, or fuel the aircraft. I've had to check the oil once or twice due to unscheduled landings, and even with that class, I would call back to maintenance if I ever had a question.
I'm assuming since they are Southwest 737s, that we're talking about CFM-56 engines. It just so happened that I flew an airplane in the AF with 4-CFM-56s, so I'm somewhat familiar. It's been a while, so my numbers may be off, but I do remember that you had to check the oil in those engines pretty quickly after shutdown (within 10-15 minutes) for the sight gauges to be accurate. If you didn't check them within that time, you'd have to motor the engine, and then check it. It sounds like (if this is even true) you parked an airplane, offloaded pax and bags, topped off potable water, then eventually checked the oil. No way did you check it before the 15 minutes accuracy time limit was up. Especially since they probably shut one down on taxi in to save fuel.
Also, it may vary from airline to airline, but the sight gauges may not even have to be checked every flight. The pilots have Oil Quantity, Oil Pressure and Oil Temperature gauges/annunciators up front which will tell them if they are low on oil, so the sight gauges may not even be looked at. And don't need to be.
So, you went to the PIC and told him about the oil. I have many friends who are pilots for SWA, and I'll tell you this, none of them would be hanging around in the airplane if there was still hours to go. Maybe SWA does stuff differently now, but they pride themselves on the 25 minute turn. Most of their planes don't sit for hours. They land, offload, onload and depart. I'm not saying that a plane dosn't come into an airport and sit for hours, but that's very unusual for an airline, especially SWA. But I'm sure as I can be that the pilots (the ones I know) aren't hanging around in the cockpit during a two hour turn. They are running to get a burrito at Moe's and running to their next gate for their next flight. Also, I doubt the PIC was "clueless" to what an oil sight gauge is for. We know what that is (and when it can be read accurately).
What the F does "looked down the static ports" mean?
This whole things reminds me of the "hero GA pilot" story a buddy of mine told me. A good friend of mine flew A319/320/321s. I can't remember what model he was flying that leg, but whichever one it was, they were able to takeoff with slats extended, but trailing edge flaps retracted. Well, they were departing with slats out/flaps up. They gave the ding and "flight attendants be seated for departure" call. They then got a call from the back, with one of the FAs telling them they have a passenger standing up, making a commotion. Apparently this guy sitting over the wing was a pilot and he just knew that airliners needed flaps for takeoff, and therefore the pilots must have forgotten to extend the flaps and he was telling everyone around him that would listen that they were all going to die since the flaps weren't out. Up front they were debating about just extending the flaps, re-running the takeoff data with flaps extended and departing. But then this guys would forever be telling the story of how he "saved" the flight and all the passengers because of his "eagle eye" and the fact that he was a "pilot." In the end, I think the Captain told the FO (my buddy) to don his hat and go back there and set the passenger straight.
I do appreciate the value of CRM and teamwork, but just realize that you may not know everything there is about every corner of aviation just because you know you own little corner.
Shoot... that's why I'm on here. I realize that even though I started flying in GA when I was in high school and cut my teeth on GA flying, the majority of my career has been military and airline flying, and I came here because I think there are many things that the posters here who are much more well-versed in GA flying can teach me. I don't know what I don't know, but I'm willing to learn.
Sorry if this post got sloppy toward the end... I'm already on my second whiskey and it's time for bed. And if you're curious, it's Michter's Small Batch American Whiskey, and it's delicious.
P.S. I snapshotted your post and sent it to my SWA Captain buddies and get their take on it. I'll report back with their airline specific thoughts.