Well...to be clear, the "mistake" I mentioned is living in New York City itself, not by any action I personally did to the bike. NYC is full of potholes, that's why I got the insurance...because of New York.
It's been quite a while since I started this post with the air leaking out the rear. Since then everything is fixed and running smoothly. However, the process was just so stupid. I'll just break it down all the way from the beginning again.
August 2019: Air in Rear Tire keeps going out. I Call Triumph Brooklyn [not my usual dealer], and say it might be the rear tire having a nail, they agree. We order the tires, which takes 3 months to arrive.
November 2019: Tires come, they're replaced. Two weeks later I go for a ride, air is still escaping. I called Triumph Brooklyn and asked if they ever found a nail. They said no, which means that
maybe the problem wasn't the tire! They surmise broken air valve. So, I bring it in again to make sure.
They do the soap and water test [which I found out about], turns out its a cracked Rim. Through my Tire & Rim Insurance I got the wheel and labor for free, scheduled for January.
January 2020: Rim is replaced. I also told them to have the Stem Valve switched to the other side, away from the brakes for easy access, they said "no problem".
2 days later I got for a ride, air is still coming out. I was furious. I did my own soap and water test, tires seem fine, nothing was wrong. I then did the Stem Valve, and just from looking at it, they did a botched job, air was leaking out faster then before. I called them up, showed video proof, told them I want this fixed, with a new Valve Stem, and I'm not paying for anything. They agreed.
Few days later took the bike in and came out clean. From paranoia I check the rear tire and the front tire almost every day. Everything is working perfectly, rear is wonderful. Took a road trip yesterday to Storm King Mountain, went 110 down a stretch. Tires are fine, Rim is solid. The process was long, but it inspired me to get the service manual for my bike and read up on how to maintain her. I'm still new to bikes [3 years riding], and I love every moment of it. I'm actually changing the rear suspension myself. Getting 640 TS Road Wilbers.
That being said, it was a cracked Rim, its fixed!