Depends of the grade of the ammunition you're looking for.
I can reload 44 magnum for almost the same price than 45ACP with Frontier CMJ 240 grains bullets, 10 grains of Titegroup and a regular LP primer, which would run me around 7 or 8$ per box of 50.
But I can also reload 44 magnum using Hornady premium .44 XTP Hollowpoints, with 24 grains of H110 and a Magnum primer, which will run me at over 20$ per box or 50 rounds.
But remember that cheap 180 grains bullets in 44 caliber are scarce, you might have to settle for higher grade.
As for the best loader, it all depends of your current budget, the quantity of ammunition you're looking to make. You can do excellent ammunition on a Lee single stage press that costs 50$ plus a die set, but expect to make 50 rounds per hour, or but a Dillon 650 press which will cost well over 1000$ (equipped) to do the same thing, but at 800 rounds per hour.