I know there are a lot of high profile people with established accounts on Di*g*g, re*ddit, stum*ble and others that are selling their services that can get you on the homepage and lots of traffic. Where do you go to buy these kinds of services? I am not talking about just buying some automated votes, but actually getting help from the big players on these sites.

I would like to know this as well...

u mean something like piqq.us? or hxxp://subvertandprofit.c0m/ ??

No, these sites are to just buy votes. I want hire someone who is well known and has lots of friends to ad my link. They wont just ad any link, it has to pass quality control and cant look too spammy.

I ran a few tests with digg and determined the traffic does not covert well, even when CS'ing. Anyone had better luck?

The conversion really depends on what you're trying to sell. There's no such thing as non-convertive traffic, there's just the art of selling and knowing what people want. Example: Promoting SEO Tools to general public coming from an entertainment website is not going to make you a lot of money...

I believe I saw frontpage-d*gg services selling on DP a while ago so you should try more luck there. Be sure to prepare yourself for overload/downtime unless you have a kick-ass dedicated server.

I am pretty sure there is not a definite way to defeat digg yet. I looked into this a few months back, and its pretty much has to be legit. If there is a way, I have no idea what it is.

With stumbleupon this is very easy.
All you need is 10 udons from Stumbleudon(So that each time somebody else discovers your site) + Autostumble(For the bulk stumbles).

The hardest part is to pick the right tags. If you pick a very broad tag(such as humor), you will never get to the featured list. If you pick a small tag, you will get featured, but nobody will see your site.
If you pick something in the middle ground, you will strike golden, and get lots of traffic very easy and cheap.

Next thing is Adsense + CS. You will still not have too much convertions, it is stumble traffic after all, but you can expect a few clicks from Adsense, and some nice revenue from CS.

Become a hot chick, Kevin Rose is a playboy, I'm sure with the right body you could get there.

The best way is on your site to setup a php script that will check where your visitor came from. If they came from digg then you either ask them to digg you or do it for them. If you send them to digg from your site inside of a tunnel you can easily find out where and how to digg for them.

Other than that, its about natural placement. I would suggest a few tactics. One, racisim. I know, its bad. I am not saying support it I'm saying write about it. People love that crap.

Keep it simple. Your dealing with smart people and really dumb people, and hardly any in between so either target the dumb ones or the smart ones. There is no magic button though. And in the next 12 months it will get even more difficult as blogging is accepted into its own search engine rankings and so on. So spam stuff is going out the door. I'm glad. I stills ay, even as a blackhatter, I kick the teeth out of any cmpetitor who uses machine generated results. Why? I take the time to add my own flavor and influence and people are at ease with typos and mistakes they would generally make.

Just my opinion.