My first suggestion STAY AWAY FROM ISLAND OUTFITTERS!
It is ALWAYS cheaper to ship stuff from reliable gun or wanstalls (also usually comes next day)
My shopping trips to island outfitters consist of walking in needing something (shell holder, trimmer pilot etc.) and they never have stock or seem like they want to help in the least bit of finding any, I check prices on bullets, and they almost cost the same as loaded ammo, I then walk out on the phone to Wanstalls or Reliable, ordering through them for cheaper prices...
As for the kit, I find cabelas is usually cheapest and has good stock (if you know what you want, if not use a site sponsor)
Dies in my opinion are personal preference... For me I like the lee factory crimp dies more than most of the other brand's crimp dies. Other than that not much difference after that once you learn to set up dies properly and spend the time to do it. Some make it easier than others
As for all in a kit, I got mine used (from a place in Keating called Murray Charlton enterprises)
Another quick tip for you, if you want to have very little down time if something breaks, go through Murray Charlton and get Dillion, since he is a Dillon distributor any problem you have you can walk in and exchange a broken part for a brand new Dillon part free of charge no receipt needed.
That being said I am not a fan of Dillon dies for the sole reason they do not come with proper lock nuts...