As noted Trail Boss is oriented towards powder puff Cowboy loads, so for your 44 Magnum I would suggest treating your 44 Magnum a bit like an old Black Powder 45 Long Colt and accepting a load that is light recoiling and easy on the wrist.
As for Accurate #5, the burn rate is not well suited to the 44 Magnum unless you can locate some light for caliber bullets, something in the 165 to 185 grain range. With a lighter bullet you'll likely find that #5 will produce a lighter load that is easy to plink with. If that doesn't float your boat you may want to look into doing a swap with someone loading for the 45 ACP, because #5 was designed specifically for hte 45 ACP and really shines in that caliber. BTW, it also makes a nice 357 Magnum load featuring a 125 grain jacketed bullet.