My brother-in-law got me started in reloading about 25 years ago. The best advise he gave me was to stick with RCBS equipment. I am still using the same press, dies and other accessories from my original purchase. I agree with savageT, spend the money on the kit. In the long run you will save, and from what I recall from the Midway ad, it contains everything you will need to get started. The kit also includes the Speer reloading manual. I like this manual a lot, especially for the instructions. Plus RCBS has a lifetime warranty on everything except their electronic equipment. As you read through the posts on this sight you will find quite a few posts where guys broke RCBS equipment through their own fault and RCBS still replaced the items.
Since you own a Contender, I would suggest starting your reloading efforts on a straight walled pistol cartridge, provided you have a barrel chambered for one. My next choice would be a rimmed rifle cartridge, like the 30-30, again only if you have this particular barrel. The rimless cartridges introduce a few reloading issues not found in the other two cartridges.