If the ChargeMaster is on sale, jump on it. Best reloading investment I ever made. Takes minutes/hours out of the process.
Single stage press would probably be the best and cheapest route to start with. Like you said you can always go the progressive avenue later. I have three single stages and a Hornady L-N-L Auto Progressive. I probably haven't used the AP in almost 3 yrs!
Dies; I like your selection. I now buy/use Hornady CGND dies exclusively. They are great dies. There may be better dies out there, but as long as I can keep turning out sub .5" ammo for all my stock rifles, I'll stick with them.
Brass Prep; I like/use the RCBS Primer Pocket Brushes for cleaning out the primer pockets. Also, look at getting one of the Flash Hole Deburring tools. Any will do, I use the Lyman. One time operation.
Priming; I use the Lee Auto Prime Hand Tool and the Auto Prime Shellholder Set. I have two of the AP hand tools, one for large rifle/pistol and one for small R/P (saves time). I also bought the Lee Universal Shell Holder Set for my presses. Keeps everything right there together and you don't have to dig or scramble when you want to change calibers.
Over-all-length guage; Must have for tailored loads. Seating depth is a critical part of the reloading equation. I have the original Stoney Point guage (now Hornady) and use it for all my rifles.
Calipers; I started out with one digital but now have two. One set up for use with Stoney Point/Hornady bullet comparator (measures seating depth of loaded round from ogive to base), and the other for general/basic measuring. Saves time not having to take comparator on/off.
Reloading Manuals; money well spent and good reading in and out of the bathroom. Get as many as you can afford. I have Barnes, Hodgdon, Lee, Lyman, Nosler and Speer, plus I have a folder in "my favorites" called none other than "reloading". In it I have; reloadersnest.com, accuratereloading.com, handloads.com and some of the major powder/bullet companies websites (i.e., barnesbullet.com, accuratepowder.com, hodgdonpowder.com, lapua.com, nosler.com, ramshot.com). Tons of information but be cautious about using other's reloading data. Every rifle is a law unto itself.
I have been reloading for 25 yrs. It's a constant learning process/hobby and I still thoroughly enjoy it. The more you reload the more you shoot, or is it the more you shoot the more you reload! Either way I can almost guarantee you'll become a better shot through the process.
Good luck and have fun! JohnnyK.
"The only thing necessay for the triumph of evil is for good men to do nothing."