I am a reloading instructor.
Reloading - only makes sense if you shoot allot - or - you need to shoot bullets that are not normally found on the store shelf. Dropping $400 to $1200 on reloading gear - makes no sense if you only shoot 1 box of ammo a month.
A good way to start - is saving all your brass for the time being and buying a reloading manual.- then take a class or seek out someone who can mentor you on this. Once you have taken a class or learned from another person - now you will be able to make decisions on what kind of equipment you should be getting. There is no shortage of people who started reloading, got scared or gave up, and are now selling their gear on ebay or on a local for sale web page.
44mag is a ton of fun reload. First - because it is very forgiving ...... minor mistakes usually don't blow up a gun. Second - because they make lots and lots of very cool bullets that you will never, ever, find on your store shelf ....... the only way to cash in on these hard cast cheap bullets, or, high tech bullets is to make them yourself.
Start - with a cheap basic C press. These are safe and you need one anyway to make test loads. You do not want a big, expensive, progressive press - yeah, they look cool - but one mistake and you have blown up a gun or lost a hand. Me - I have 5 very trophies - First Place - because the other guy made ammo on a nice big progressive press ......and screwed it up.
A rule with no exception - unless you have it printed in black and white in a book - you do not do it. Just because BillyBob209 says he does something when loading for his 44mag....... this is not going to pay the $14,000 Emergency Room visit and the $56,000 follow up surgeries.
You very much need to have someone to show you - someone you can call and ask questions. Second rule of reloading - if you have a question, STOP! Do not continue!!
Me - I learned to reload on my own back in 1976. From a book. I only loaded 45acp target rounds - 45acp is another forgiving cartridge. It was not until I moved to Kodiak Island, Alaska in 1986, the locals shooting club had lots of reloaders and handloaders - this is when I learned how close I had come to disaster.
If you are shooting 700 -900 rounds of 44mag a year....... you should consider reloading with basic equipment. C-press, carbide pistol dies, manual scale, manual powder thrower, vibration case polisher. If you buy 240gr hard cast lead bullets in bulk - that equipment will pay for itself in 18 months. If you are shooting premium jacketed projectiles - 700-900 per year - the equipment pays for itself in 3-4 years. Now, if you learn to cast you own bullets from scrap lead - now you can drop the cost of a 50rd box of ammo to just under $3.75 a box. Most of the cost is the $.05 per round for the primer.
Starting reloading - you need unrestricted access to a place to shoot. You will load up 20 test rounds, fire them - look them over. Adjust the load, make 20 more, then head out and fire them. When you have a load you like - you make 100 - try them. If you still like them...... now you make a big batch. You have no idea how many times I have seen a guy show up at the local range - all smiles because spent all Saturday making half a 5 gallon bucket of bullets!!! And of the first ten half don't go bang, or, they go pfutt and the lead gets stuck in the barrel!! LOL. Now, the guy will spend the next two weekends - taking all those bullets apart so he can at least salvage the bullets and powder.