After finding large chunks of what looked like rocks in my drain and some research, I figured out that the flange arm must have corroded and broken. I ordered the parts (and they showed up very quickly) and tore everything apart. It only takes about 30-40 minutes to get the washer ready to start pulling the tub out. It took and hour to get it out and split the tub and get everything cleaned up enough to put the new flange in. One thing to note is there was a washer on the flange i pulled out that wasn't present on the flange i ordered (it goes on the axle after the o-ring). I wasn't sure if I was supposed to reuse it or perhaps the design changed, but after inspection decided to re-use it and it appears to have worked fine (I also didn't see a part number for that washer specifically).
Also, be absolutely sure to order 6 new bolts with the flange, I'm glad I did because the head snapped off every single one when i tried to remove them.