i would actually recommend 9mm or 45 ACP over the rifles to start. rifles has lubing/cleaning, more measuring and the dies are trickier with the neck.
9mm with unique - cheap, there is NO way you will double charge a case with this powder, measuring is easy and you don't need much of a crimp. higher pressure round though, so if you miss your crimp entirely it's more dangerous. but you've read the manual and know enough to check the rounds before you put them into the magazine
45 ACP - a bit of a trade off, since you CAN double charge a 45 with most powders. however, it's a lower pressure round so if you do get a small amount of set back chances of you blowing anything up are smaller.
do NOT start with 40/10mm/38 super or the more exotics. bad news when gettin the feet wet.
also - even tough you can buy a good turret or go balls out on a progressive i recommended you START WITH A SINGLE STAGE PRESS!!! even if you move quickly to a progressive, the single stage gives you a firm appreciation for all that goes into reloading. it will help teach you the extra patience you will need to discipline yourself to have doing this. plus, you WONT get rid og the single stage - it has a million uses. loading short runs to try new loads, using it when hand measuring power for working up loads, for pulling LOTS of bullets when you mess up (not that i know this for experience of anything

) or for pulling someone ELSES reloads you got in that sweet trade deal - which you are NOT going to shoot because it's dangerous and you want to use the components.
i started with the 9mm/unique combination. i didn't have any issues and you will learn SO MUCH the first couple hundred rounds you load.
it didn't take me long to get into 45 ACP and a progressive press and have THOUSANDS of reloads under my belt within 6 months. i pulled a lot of triggers working up my loads - slowly and methodically - it took me less time because i was really excited and was at the range once every three days
good luck, i hope this helps - ask a LOT of questions, don't get dicouraged and if you need help ASK!!!!
good luck!!!!!!!!!!!!!!