I can't tell you the best way to start, but I can tell you how I chose to start.
I waited for a used press to come up for sale on glocktalk/thehighroad/1911forum/m1911.org/northeastshooters/sigforum/smithwessonforum
Can you tell I browse many different classifieds? Two or three come up for sale each month, when you get into the 500 dollar range they start including things like tumblers and scales. Glocktalk's Misc. gun stuff forum seems to be veritable reloading treasure trove.
320 dollars got me a 15 year old dillon square deal B with 9MM, .45ACP, and .357/.38 special dies. Value wise the dies are about $100 a piece, the press runs fine and Dillon sent me some replacement parts no questions asked. I paid more than you have to... you could step up to a 550 or 650, but I wanted the SDB because of the auto-indexing (less likely to double charge). At some point I will by another SDB so I can have my two high volume calibers ready to load immediately, I can also pick up dies for an infrequently shot caliber (I am thinking .44 mag) along with the press.
I bought the Speer reloading manual which was mostly useless as I gathered my information from forums and it doesn't have loadings for many different powder/bullet combinations. I have the Lyman manual incoming. I bought a Lee safety scale for 12 dollars (more than adequate, consistent and accurate).
The biggest expense after that was the vibratory tumbler which was on sale at midway for 70 or so dollars, I got the Frankford arsenal model, it came with media, polish, and a bucket and media separator. Great deal. I also got the RCBS kinetic bullet puller (there is actually a picture of it in the speer manual) along with a GOOD pair of calipers. I recommend good calipers, so much easier to read and work with, dial is fine, don't see why people find it so hard to use. I bought a pair of sears craftsman dial calipers, I overspent 10 or 15 dollars in my estimation.
Information wise, I read many forums and have a knack for distinguishing between facts that I know to be true and those that might be true but need verification... I am also having a pretty easy time diagnosing issues in the press and adjusting things, It seems like such a simple natural process unlike say... the operation of a locked breech pistol under recoil.
Some links:
Press:
http://glocktalk.com/showthread.php?s=&threadid=618169
Manuals:
http://www.midwayusa.com/eproductpage.exe/showproduct?saleitemid=823498
http://www.midwayusa.com/eproductpage.exe/showproduct?saleitemid=636126
Calipers:
http://www.sears.com/sr/javasr/product.do?pid=00940778000&vertical=Sears&BV_UseBVCookie=Yes
Bullet puller:
http://www.midwayusa.com/eproductpage.exe/showproduct?saleitemid=630146
Tumbler:
http://www.midwayusa.com/eproductpage.exe/showproduct?saleitemid=816895
http://www.midwayusa.com/eproductpage.exe/showproduct?saleitemid=668307
You should also look into finding a good bench to mount it too, this is very important, you may also need a large number of bullets to help weigh the bench down (I do).
Regarding the cost of reloading, 9 cents a round is a good benchmark, you can do less (I do). I only need 3 grains of powder for my mousefart 147 grain 9MM load.