Alright! Update time.
Upon loading and reloading some mags over this week to test a theory (as well as receiving the 17rd Staccato mag) I found that using an UpLula causes the rounds to nose dive into the inside of the mag and press against it, making the rounds stick as they come up. Today at the range I tapped the mags several times to make the rounds move back and sure enough, that fixed it. BUT.
I haven't had this issue with my other mags for other guns I have. SO! I hand reloaded both the 17rd and 20rd SA mags and made sure to press the rounds all the way back, but DID NOT tap them to move the rounds back (was testing to see if it was an UpLula only issue.) Some of the rounds, would STILL nosedive into the inside of the mag and cause sticking.
When I hand reloaded and tapped them down to make sure the rounds were seated back properly, ZERO issues.
I repeated this process with the Staccato mag and had ZERO issues, regardless of hand reloading, UpLula or tapping.
So... for whatever reason, the SA mags seem to have an issue with rounds pressing forward and rubbing hard enough on the inside to cause the rounds to stick sometimes.
Side by side, the Staccato mag interior is very slick and smooth, almost polished looking. The SA mags are not exactly what I would call smooth and you can feel the difference with your finger.
In the end, the staccato mag worked without ANY issues no matter the scenario, and the SA mags worked only if you tapped the mag after loading to make sure the rounds were seated back.
Unrelated note: They had a Wilson Combat EDC X9 4" at my GS and boy was I tempted to pick it up for my carry gun. It was $150 LESS than normal price too. Still a pretty penny though.