I think what happened was that the grid snapping was sneakily getting in the way. Short version: after making sure all the big component pads (those TO220's) were on a 25mil grid, then I had no trouble routing the 100mil trace all the way up to the pad.
It so happens that the TO220 on the right in the pic was "properly" on grid, while the left one was a tiny bit off. By which I mean that they were actually both OFF GRID XD, but one just happened to luck out location wise and the other didn't.
Anyways, 100 mil traces worked out fine with all DRC rules passed (10 mil clearance) and gerbers out the door to itead.

Onwards to the next pcb...