If your new, start with something simple and learn the basics. Like everyone says go with a single stage. I now use a dillon 650 to load with, but my rock chucker still gets some work to do now and then. I wouldn't think of using my 650 to pull bullets with a collet style puller, this is the main reason I keep the Rockchucker: to pull bullets. Sometimes while doing load development, I'll have a load/bullet combination that I can just tell isn't going to performa or it is already looking too hot, so I'll just quit with that combo. I'll go home, pull the bullets with a collet style puller and try a different combination. I use the rockchucker for other uses too, so it is still earning its weight in cast iron.
As far as weighing every charge, that depends on the gun, the powder thrower, and you; plus, a few other variables thrown in that I cannot think about right now. I have some loads that shoot good without being weighed and some that must be weighed. It all depends.
I started reloading to save money, and I do save a lot of money. Howver, today I reload for accuracy and this hobby gives me the opportunity to fine tune my loads for each and every one of my guns. Go price 5 boxes of Federal Gold Medal Match ($165 for 5 boxes at midsouth). Then price a box of 100 168gn sierra match king ($30 at midsouth), a bag of hornady match grade brass ($60 per 100), a pound of H4895 powder ($20 at the local gun store, and a 100 match grade primers ($3). The total cost of the componets listed above runs $113. However, you should only figure $12 for the cost of the brass since you will be reusing the brass at least five more times if not more. You will also have about 5 oz of powder left after loading a 100 bullets too. That brings the cost of reloaded ammo tuned for your barrel down to almost 1/3 the cost of equivalent ammo.
Today, I have a bunch of remington and winchester bulk bullets in inventory that I'll probably never shoot. I'm always working with quality bullets like Sierra, Nosler, Berger, etc. because they perform better. If you want accurate reloads, buy quality bullets. The quality of the bullets you use and the quality of reloading that you do will be the two most important things you will learn.
Welcome to the sport