I'd start with die adjustments--
It sounds to me like your powder-through-expanding die is not set to make a big enough 'funnel' at the cartridge top.
1. Did you set the resizing / decapping die to make firm contact with the ram fully up, then add 1/4 turn turn and tighten the die nut?
2. With that die in place, and with the ram up, adjust the powder-through-expanding die this way:
first, screw it down to make 'firm contact' with the ram; then,
back it out about 3/4 turn. Now, screw down the die nut.
Try running a case through the decapper-resizer, then through the PTED. Take the case out and look at it: is there a 'noticable' flare to the top? Enough so you can set a bullet in the flare, and it drops in a bit--like 1/32", and sits square?
If those two dies are adjusted correctly, then set up the seating die again: Assuming you have a 4-die set, did you first back off the seating stem, then set the die to ram contact and then back it out three turns?
Etc., etc.
I don't yet reload 44mag, but it does appear you have the correct (lead) bullet diameter. Somebody else will check in on the bullets, I suspect...
Jim H.