Remember one thing, if it was hard most of us couldnt do it.
Reading is a good thing. A mentor could be a good thing.
Could also be a not so good thing depending on the mentor so be careful there.
Learning the basics is all you need to know for now, or ever know depending on you and where you want to go with it.
Id be ruling out any progressive loader at this point.
Dont hesitate buying used stuff on ebay. That includes dies etc. ive bought lots of used dies on ebay.
An rcbs rockchucker press wont ever be obsolete for you even if/when you ever add a progressive.
Get yourself a decent set of dial calipers, less than $50 will do, but best not plastic.