Knowing what I know now back when I started out wouldn't change much of anything.
I started out helping my pop load his rounds as far back as I can remember, but it was sometime around the late 60's. As I grew, I also became more interested in shooting and as such he got me started loading my own bullets when I was around 8, (he kept a VERY watchful eye over my shoulder. )
That all said I hit my stride in my mid 20's when I got into shooting my handguns for hunting. I shot easily 2-300 rounds a week through several revolvers. I then would load up all my empties on the weekend using the old single stage Wells press.
I managed to purchase an RCBS 4x4 back in the early 80's and stil have and use it for bulk ammo, but I still load more rounds on my newer RCBS Rock Chucker.
So as for what I know now that is actually relevant, I would determine what my overall goal was to start off with. If hunting, target, or simply plinking loads were going to be the bulk of my work.
Once that was determined I would purchase at least three different manuals, as well as download as much available manufacturer load data as I could assemble for the calibers I would be loading. Once I had this info I would put together a list of the top recommended powders for the loads I intended to use. This would be further culled down into the one or two powders which would cover the most loads for each or all calibers. While they might not be the utmost in velocity in some or accuracy in another, it would still allow me to load for more than one caliber with the same powder.
I would also do a similar thing for the bullets I intended to use, culling the variety down into a smaller and smaller lot until I had only one or two listed to accomplish my intended goals.
As for equipment I would go with one of the above recommendations on picking up the complete kit which would have just about everything in it I would need to load. I would still need the dies in most cases and would probably pick out a set based upon user reviews or customer service in case I ever needed any assistance.
When I had everything narrowed down I would look around at the numerous on-line supply places and try my best to get everything I could from one vendor. Just a LOT easier if there is a problem and I need to return something. With the components, I would probably look locally to see if I might be able to find what I had picked out and purchase a one box quantity in order to do load development. Once I found I either liked the particular combination or not I would not be stuck with a large number of components I probably wouldn't use. Once I DID find what I wanted, I would most likely purchase powder, primers, cases, and bullets, if possible in bulk. If the powder was good across most if not all I was loading I would get it in an 8# jug, primers in 5K lots, and brass in a lot of 500 for each caliber.
Just as a "for instance", I did almost this exact thing and ordered an 8# jusg of H-4895 as it was the most versatile powder that I could use across the board with almost every caliber I load for in one form or fashion. It might not be the top end performer in some, but in others it is, and to be honest I haven't found any of them that I didn't get an accurate load as a result of using it.
So there's my .02, it worth every bit what you paid for it.
Mike / TX