I would recommend looking at the RCBS Rockchucker reloading kit, for about $260. It comes with the Speer manual. You would still need to get a case trimmer and of course, dies and shell holders for your calibers.
If I were to start over I would get the Forster Co Ax reloading press, for about $230. Heck, I just bought one as an additional press. One of the best things I bought myself for reloading was the RCBS Chargemaster Combo for about $280. It takes all the effort out of getting the right powder charge in each case. You did not say that you were on a tight budget so I mentioned this. I recommend Forster and Redding dies, Hornady if on a budget.
I have only used the Forster case trimmer as it has always worked well for me. There are some other good ones out there, I just do not have any first hand information on them.
Hornady did a recent article on reloading vs buying store bought ammo and they said that you could reload for just over 1/3 the price of loaded ammo, after you have the reloading equipment.
You can really speed up the learning curve if you can go to a friends and watch them reload. There are lots of people here that can help you out with reloading questions, you just have to ask! I wish that the internet was around when I started as I had to learn everything on my own. Yes there was TV, but just black and white!
I hope this helps, along with all the other good advice you have already received.