I'd suggest the Lee 4 hole turret press as a starter. Midway has them reasonable with everything you need except powder/primer/bullet.
http://www.midwayusa.com/product/785993/lee-classic-4-hole-turret-press-deluxe-kit Still need to get the dies and shell holder, I use Lee's 44 Russian dies and a 41 mag #9 shell holder.
I get my 44 colt brass from Starline, good brass and reasonable cost.
I looked at Midway and the cheapest they list 44 colt loads for is .78 cents a round. I cast, but figured buying 200 grain bullets @ .09 cents a round and new cases and they would cost me .32 cents a round. If you reuse the brass, cost goes to .14 cents a round. Thats for smokeless with Titegroup powder. If you get into casting the price drops even more, but you can see anyway you go it's a good savings over .78 cents a round. Price for black powder loads is a bit higher due to using more powder, but at about .40 cents(new case) still cheaper than Goex black dog ammo at .82 cents a round. One other thing you need to reload is a way to clean cases, like everything else you can go cheap or expensive. I like we tumbling with stainless steel media, and for small batches I use a harbor freight single drum tumbler. Some people even just soak in water and citric acid and it seems to work for them.
Of course you don't really save money reloading, you just shoot a lot more.
I've got 5 presses, two loadmasters, a pro-1000, a 4 hole classic cast turret press, and a single stage. While I still use the single stage for some operations, if I could only have one press it'd be the classic cast turret press. I should say 6 presses, my first foray into reloading was a lyman 610, kinda like a pair of pliers with proprietary dies, slow and irritating, but showed me that reloading is easy and fun, but I don't count it as it's been sitting in a drawer for the last 15 years or so.