Update: Master Achievement!
After grinding away on the online ladder and watching an RNG shitfest, my character finally broke out of the 250 rank wall. The strategy provided with Chiba Sanako and a YYYAYYY spam became much more effective. I finish writing this ranked 77 with 1604 points.
Final Record 127W:67L a 65% Win rate
With this out of the way, I see the end in sight.