Phrag Repotting Questions

[WaterWitchin]

Need some assistance. I'm repotting a phrag that is much larger than any I've ever repotted. Have cleaned it up pretty well, and don't want to divide.

When unpotting, the roots were a wound up mess (waited too long). Also, I've only been growing a couple of phrags so not much expertise.

Should I trim back more live root? And shown in pics is the pot it was in. Bigger pot? I can't imagine getting enough medium into the pot plus stuffing back all these roots.

First pic is lying on side, second upright.

Any advise would be greatly appreciated.