After I parked the bike, I noticed a couple of small oil drips under it where there hadn't been any before. The good news is that based on the amount of grime buildup, there has been an oil leak for some time and unless I really push the engine, it doesn't leak enough to lose much oil. The not so good news is I was about a half quart low. I checked the sight glass after it had been sitting a couple of days and the oil level was below the window. I warmed the engine, shut it off and checked the level 5 minutes later and the oil level was at the bottom of the sight glass. I added a half quart of oil, warmed it again, and checked it again after 5 minutes and it was properly filled to the upper 1/4th of the sight glass.
Side note - I know the sight glass is questionably accurate, but I think it's designed to be used the same way I'm supposed to check the oil in my 2015 Jeep Renegade - warm the engine so the oil is at operating temperature/expansion, shut it off, give it 5 minutes to drain, and then check the level. After a certain amount of cooldown it will no longer give an accurate reading. In my Jeep it's because they use the 0w-20 engine oil as hydraulic fluid to run the Multiair intake unit, which hydraulically/electronically adjusts the intake valves per stroke, and there is a secondary oil reservoir that feeds the hydraulic pump. It's really easy to get an incorrect oil reading if you check it like any other car (cold, in the morning before starting like most cars always have) because you have to ensure there is enough oil to fill the secondary reservoir and it takes a weird 5.5 quarts of oil to fill, so some lube shops give it back to people half a quart low from the start. Add the fact that the engine is an Italian designed oil burner and you get angry drivers who didn't know how to check their oil properly and learned it's been low for a good while. Or those owners who never check their oil and find out it's REALLY low when they push their oil change maintenance back since they used the 10k mile synthetic stuff. FCA says the acceptable oil burn level for the 2.4L Multiair engine is 1 quart every 1000 miles until 50k miles, then 1 quart every 750 miles after 50k miles

I need to degrease the engine to find where it's leaking from, but it looks like I may be getting leaks out of two common spots - the oil sensor below the sight glass, and something near the driveshaft area. I'll be diving deeper to find out exactly where soon enough, but for now it's on the list. Also on the list - when I got the bike, the rear shocks were low on pressure, so I pumped them back up to about 32PSI. They leaked a little bit of air so I pumped them back up before the ride with my brother, and when I did my inspection afterwards I found that my left shock is leaking oil. I have read that there aren't really any serviceable parts in the shocks, so replacement is the only way to go. For fun I just tried to see if OEM shocks are still available and I can buy two sets of Progressive 412 shocks for the price of one OEM shock

Last night, I also pulled my top triple clamp to make sure everything was tight and lubed. I followed along with a video I found of Don from the NorCal Voyagers so it was pretty easy overall. The bike's PO had Progressive springs installed in the forks and whoever did the work did a pretty good job based on the tips Don gave in the video, though they didn't move the DIN connectors in the fairing during reassembly so the inner fork-side fairing cover didn't seat deep enough and was getting scratched by the fork bolts whenever you would turn the bars to the right. I was able to get them pushed out of the way but the scratches are still there. During reassembly, I really noticed how tight the ignition wires and wires going to the left handlebar control assembly were. Even after I cut the left frame zip tie, they start to pull right before full right lock. Is that still normal, or should it be smoother than that? I plan to take the fairing off next week and play "grease the electrical contacts" at least so maybe I can get some more slack in the harness.
I also saw that the speedometer cable gets caught when going full right lock if it's routed between the forks. It gets pushed by the fork until it starts making noises against the rubber insert in the fairing. I re-routed it to the outside of the left fork, but it seems to get caught just about as much on full left lock. Is this something to be concerned about?
Finally, the left brake caliper on the front wheel seems to be a little tight, it makes a little noise when I spin the wheel when the front is jacked up. It doesn't seem to be too big of an issue and the pads appear to be OK still. I'll be working my way through these issues, plus going through the Periodic Maintenance listed in the service manual, so surely I'll find more things that need work as I do!