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Having used the Lee I will answer some of these questions as to what I do.
1. No problem with auto indexing
2. I use factory crimp die
3. I use auto drum powder.
They sell a kit at Midway
https://www.midwayusa.com/product/78599 ... deluxe-kit
Has some stuff not in Kempf kit and some stuff you wont use much. For Lee kit I recommend also getting the mounting plates to mount to your table, extra turrets, extra drums for the powder measure, an electric scale, and when you buy dies ( I use Lee) make sure you get carbide and make sure you get the ones with the factory crimp die (deluxe kit). Also I like to get case gauges for every caliber I reload. One extra die, the Lee universal deprimer die. Having the Lee scale is a pain but very accurate and you can make sure your electric scale is accurate. Then you won't use the lee scale again. For cleaning brass I like the kit Cabellas sells of a tumbler comes with media and cleaner. Works good. Ton of other stuff you will need. Have fun.

I started with a single stage and moved on to a Lee turret. I guess it really depends on how much reloading you are going to do and how much you want to spend. I go for months at a time between reloading and then reload a couple of hundred rounds. Some people reload hundreds every day. If you are going to be a high volume reloader than go for a progressive. If you are going to reload a couple of hundred every now and then get a turret. I would search youtube and see how others use their press. I just don't reload enough to get a progressive. If I did buy a progressive I would stay away from Lee though and probably go to a Hornady or Dillon. When you start adding in bullet feeders, different plates for each caliber, case feeders and all of the nifty toys that the progressives need it can become expensive. I also think that the progressives need more safety checks because it is easier to screw up. I believe that most progressives can be used as if they were single stage as well so if you are planning to be high volume you can start out slow and work up to progressive. All is a lot of fun.