I think they might move with a 3/8" final pass.
I don't think you need to pocket the waste. I occasionally cut stuff like this without breaking any bits.
I conventional cut everything, so that any waste material is pushed away from the part when it's cut loose, so the bit won't grab it.
On the small parts on the upper right, I'd cut them from right to left, with the start of the cut on the left side near the bottom. You want the parts to be attached to the sheet as long as possible, so they can't move. By working from right to left, each part is fully attached to the sheet along the left side, until the end of the cut. The scrap material will just fall to the side when it's cut loose.
I'd do the same with the longer parts, with the start of the cut on the left side near the bottom.
I've never used a 1/4" compression bit, so I'm not sure what the best strategy would be. If time is not an issue, maybe two passes leaving about .02" for a finish pass, and leaving a thin onion skin, than a final finish pass all the way through, at a lower feedrate.