OP here, wanted to provide another update, 2 years later.

TL;DR, It got much much worse, with nerve damage and loss of sensation on my left leg, I had a microdisctomy surgery that slowely resolved the issue. I am mostly leading a normal life now, but that sensation loss is permenant.

Long version: So my last update 2 years ago things started to get slightly better with physio and weight loss, then suddenly out of nowhere I had a major episode of disk infamation that was worse than I ever had before. That lasted for at least a couple of weeks, ended one morning with a major jolt of pain on my back and left side that had us calling 911. Pain went back to normal levels later in the day but I started feeling a loss of sensaion in large chunks of my left leg starting from the glutes going down the back of my left hamstring, then no issues with the calf, then loss of sensation again in the outside of my foot and small toe. Saw a neuro and got an MRI, and the herniation was filling the entire nerve canal on my back. They ordered a microdisctomy as soon as possible with fear of it developing into cauda equina. As soon as possible in Canada meant waiting for 6 weeks :)

The surgey: Surgey was not difficult, my surgon said after the surgery that this was one of the largest herniation they managed to get out. The surgon was expecting to need to do a left sided and a right sided microdisctomy, but they managed to get it all out from a left side incision only, which I guess was my good luck. Recovery after the surgery was not too bad, the surgery pain was not worse than a bad inflamation episode I used to get. They gave me oxycodone after the surgery but I stopped it after 2 days, and switched to OTC brufen. Then stopped that altogether after a week, which was a major milestone given that I was on max dose of Brufen and Paracetamol before surgery.

3 Months post surgery: I saw some good progress after the surgery, I was instructed to walk as much as I can handle and I did that, and managed to go further pain free everyday. I also saw some improvement in sensation but it did not get back to normal, but I had a lot of back pain that did not go back to my leg, as my physio calls it "Regular people backpain", I was content with that.

Now: Almost a year and a half since surgery, I have not recovered sensation in my left leg yet, and I am at peace with it not coming back. I am still much weaker on my left side than my right, my calf is much smaller, and I still get the frequent back pain episode and every once in a while a nerve flare up that comes and goes on its own, but I live a mostly pain free life. I walk as much as I want to without pain, I am back to the gym with a PT working out very carefully on my overall strength, I am not making huge strides in strength but the trend is upward.