xdeano, that's a good list. You're going to need a trigger too.
I'm not sure how significance the difference would be in this, and someone with more experience can chime in, but I don't think you should have to wait 6 to 9 months for a barrel unless you want something that's out of the ordinary. You can order barrels from Grizzly.com or Southern Precision Rifles (bugholes.com) and a few other places I'm sure, and they have quite a bit in stock. Somebody mentioned earlier that Kreiger has barrels in stock. The only reason I can think of for getting it from the manufacturer is the price may be a little better and it can be fully customized, but there may be more to that.
+1 on Stockys for the stock, and if you're going with a Rem 700 footprint based action, then you should be able to find one in stock somewhere. On that note, you don't necessarily have to stay with an actual Rem 700 action. There are others that have the Rem 700 footprint, and that's what there are a lot of parts (stocks, bottom metal, etc) for. It'll give you lots of options for sure. I know Stiller actions have the Rem 700 footprint, and they're probably one of the least expensive of the custom actions. A couple months ago you could get a Rem 700 action, blued, from Brownells for $450'ish and it came with a bolt. But you have to buy recoil lug and rail. A Stiller comes with both of those. Little things like that you'll need to keep in mind. Also, your magnum bolt face will probably cost more and be harder to find as previously mentioned. I started off wanting a 300 Win Mag, but Russell steered me towards the 300 WSM, one of the reasons being the short action gives you more options in the future should you decide to have it re-barreled and chambered for a different cartridge.
You threw out a $2000 budget number (not including gunsmithing), and that's a little thin for a true custom rifle, but it can definitely be done. That being said, be sure to check the "Options and Accessories" board in the classified forum religiously for the things you know you'll want. You can always get the stock painted the way you want, and your gunsmith can do any additional inletting for action, barrel, trigger should the need arise on a used stock or chassis. Triggers pop up on there periodically. I'm currently in love with Huber triggers, but I see Jewell, Timney, and old style Rem 700 triggers appear, but stuff usually goes pretty fast there. You could get every single part you're going to need for under a total of $2,000 from that board, except the action which you can get from the Firearms for sale board.
Someone else mentioned calling GAP or somebody like that to ask questions, and you said: "Probably should have thought of that one myself- I just didn't want to waste anybody's time unless im ordering something right then and there.... but I don't know whats good to order.... and salesmen do sell their own products..."
Most gunsmiths are simply assembling parts from other people. Really, the most important thing they're doing is cutting the chamber (somebody correct me if I'm wrong). Of course, it's important that they put the rest of the parts together correctly, but the chamber is what you're paying for. So you wouldn't have to be too overly concerned about them only suggesting "their" parts. I could be wrong on that, but at least the ones I've dealt with didn't give me that impression at all. And for most of them, it is part of their service. Mind you, there are those that would prefer not to deal with a guy that's getting his first custom made and doesn't know what he wants yet. I'm pretty sure they would let you know that though.
Be sure to wear out the search function on the Bolt Action Rifles board too. You'll find a ton of information, and you can start to educate yourself. Once you've learned a little, then start a thread about your specific question. Just be sure to be specific, and make it very obvious that you've already done searches and researched prior to starting your thread, and you'll get the most favorable responses (in my experience at least). Everybody here loves to talk about guns and give their opinion. Soak as much of it in before you start making any final decisions. You'll be glad you did.