Welcome to the forumand reloading. Thanks for asking our advice.
What rcmodel and Honest John said is spot on.
Trail Boss powder is very forgiving. BUT DO NOT COMPRESS THIS POWDER. Otherwise, it is impossible to get overpressure. It runs at a decently low pressure and occupies a lot of volume, making it easy to see in the bottom of the case. It is great to learn with.
I don't recommend loading for full power while you are learning. So, you don't need really hard cast lead slugs if you stay under 1,000 fps. (Loading manuals will give an estimate of velocity to expect.)
Use a mallet to drive the loader. Do not use a steel hammer unless you pad the face. A wood mallet, rawhide, plastic, hard rubber or brass will do better.
Get a scale. The Lee Safety Scale is accurate and once you get used to reading a vernier will do you just fine. Being able to get known powder charges will enable you to vary your power level and expand your powder choices immensely. And it only costs $33 from Lee Precision (and less from other retailers) and far less on the used market.
If whacking on explosives (the primers are explosive, the gunpowder merely flammable) is unnerving to onlookers (or to yourself), a hand priming tool is available from Lee Precision, too. Consider it. Otherwise, wear a glove on the non-hammer hand and use eye and ear protection. I have never set off a primer loading with the Lee tool, but have testimony that others have done so.
Prime an empty case, load into your 44 and set it off. You will see how loud it is. For extra information, drape a paper towel over the muzzle to see how much power there is and do it into a porcelain sink or clean dropcloth to see what residue comes out. You don't want that embedded in your fingers or eyes. The ear protection mentioned before will protect your ears from the extremely rare primer detonation as well as the constant banging (at east 5 or 6 whacks per cartridge loaded).
I own, and have used a Lee Loader (also known as the Lee Hammer Tool, Whack-a-mole or Whack a bullet) for all of my cartridges. But use a press. Much quieter, faster and does not take up much more space or cost much more, really.
Once you add the accessories that you REALLY SHOULD USE, like Scale, calipers, various sized powder dippers, bullet puller, notebook, dropcloth etc and a box to put it all in, the Lee Loader is not that much more compact or inexpensive than a press setup. That's the sales pitch.
Enjoy your Lee Tool. Get ABC's of Reloading (from your local library, maybe) and a couple of loading manuals (not just for the load recipes, but for the instructions they all have in the early chapters, too).
Merry Christmas
Lost Sheep