My suggestion might be a little different than some of the others you might get... but if you are just starting off and trying to build up your tooling I would strongly suggest you concentrate on used tooling and Craig's List is your friend! You can also get some good used tooling on eBay, but it will probably cost you more, because it gets a lot more exposure to people who knows what it's worth.
I've bought from them all... eBay, Shars (both on eBay and their website) Amazon, Enco (I LOVED Enco), etc. etc. etc.. The best value by far was checking Craig's List and jumping on stuff that comes up. You can even save searches that trigger an email notification when items come up so you can jump on them quick. Do a search for "machinist tool" and see what comes up.
There is a huge difference between the import tooling you will get for cheap prices new on-line and the used/new stuff you might get from ads from people that have left jobs, need money, are retired or just cleaning out, etc.. There is no comparison between good ole american brands like Cleveland, Niagara, etc. and most import stuff. Sure, the import stuff is HSS, but not the same grade as most US made tooling. It just does not compare.
A lot of guys leave jobs or retire and they end up with a lot of tooling in their tool boxes from work. They are usually willing to sell it for a very decent price since it didn't cost them anything in the first place. You might even benefit from running a wanted ad in Craig's List. You never know what might show up. If you have time, I suggest you go this route. One purchase alone and you might be lucky and end up with a very healthy supply!
Good luck,
Ted