You should go and check out a local Vintage match too... just to see how they are conducted... and to see how much fun they are! 

As for progressive presses, my feelings are this:  if you are loading a thousand rounds of pistol ammo a month, then get one!  If you're loading a couple hundred rounds of Rifle ammo a month, they are (IMHO) totally unnecessary!  I load (on average) 200 to 250 rounds each month to support my son and my self with three relays per match a month.  I do all of this with my 30+year old LEE Challenger press at a rate of around 100 rounds per couple hours, after work in the evenings.  It does me well.  Heck, My press doesn't even have the quick change die capability that the newer presses have!  Oh, and just in case you were wondering, I load for 5 different rifles calibers (30-40 Krag, 30-06[1903A3], 30-06[Garand Rifle], 7.7x58MM[Arisaka], 7.5x55 Swiss[K31]), and 6 different pistol calibers (.45 ACP, 9mm, 38 Special, 357 Magnum, 44 Magnum, and a very rare 10.4mm Italian Ordnance [I have to convert .44 special brass for this]).

Also, with regard to those automatic charge devices, many use them with great success... but I am just a little too OCD, so I weigh each and every charge (if something went wrong and I blew up my Krag because I got the charge wrong, I have no one to blame but myself... and I'd also never forgive myself!).  Also, you have to clean them very carefully when changing powders.  One grain of Bullseye in with a charge of 4064, and it's goodbye Charlie!

I think the main reason Carbines are not used has to do with the sling.  An "As-Issued" Krag carbine would not have sling swivels, and most of us use the sling for position shooting (they are not permitted for off-hand/standing).  However, if you're good, it wouldn't be necessary.  I would think the Carbine would have the advantage in Off-Hand, as you wouldn't have that heavy 30 inch barrel to heft and steady for each shot.