Since you probably aren't going to be loading hundreds of rounds at a sitting for a .44, a single stage press is good. Carefully choose your equipment. Different manufacturers have different philosophies on how to build equipment, and since you are going to be repeating the reloading steps many thousands of times for the life of the equipment, something that's a minor annoyance or slightly slow you down will cost a lot over the long haul.
Personally learned points: A digital scale is nice! Saves lots of time and frustration. Make sure your press has a way to catch spent primers. A tube with a jar setup is best. A tray setup is OK, the ones that kick it to the floor really sucks. A case cleaner is a must. Yes, you can shoot black sooty loaded rounds, but really? Spend a couple of bucks more for plated bullets to lessen lead exposure. Pick a powder that will flow through a volumetric powder measure nicely. Flake powders tend to bind the rotors. Check loading manual and load for economy, not super hot magnum danger rounds. There is invariably going to be some variation on your loads, and you want to design in a safety factor.
Who knows, you might start to enjoy the reloading process as much as the un-loading process.