Talley - first go to a store that has the reloading items out to view.
At most, used, you should be in the $300 price range, MAX, for QUALITY, used reloading components.
I recommend starting off with a single stage. You will ALWAYS need a single stage on the bench anyways. Check Lyman's site, they have refurbished Orange Crushers for $65
http://www.lymanproducts.com/store/page166.html
These are are on the same grade as an RCBS Rock Crusher or Redding Boss.
Case trimmer - Lyman's is good - don't need shell holders. Old or new style RCBS are great. Forster are great as well. Currently have a Hornady - but would not purchase again - have to use their shell holders (larger center hole), but it works well. I drilled a couple of common shell holders to work in my Hornady trimmer - need a nitrided bit and a bench mounted drill press - shell holders are HARD - use plenty of coolant/lube and drill on slow speed!!!
Powder measure (recommend the Hornady with the micrometer adjuster - you will cuss the others) - Lyman #55 is good as well.
Scale - Hornady magnetic scale (longest beam available) or an RCBS 1010. I tried two RCBS Chargemaster combos and two Lyman DPS II 1200 - don't waste your money. Not as accurate, sensitive to external and power supply, and slower than using a manual powder measure and scale.
..and a tumbler - Midway has good deals on the vibrating tumbler, bucket, and seperator. Dillon CV500 would be my next choice - but spendy.
Highly recommend Redding dies, cost a little more but. RCBS, Hornady & Forster are excellent. The Forster Benchrest seaters are awesome.
Digital calipers - buy them at harborfreight - same as what everybody else brands their calipers as...but only $16....versus $38!!
AND buy SEVERAL reloading books. Read them...and then read them again. I have 9 reloading books.....and want more!