I don't think my approach would be very different than what I actually did:
(prices are from memory and probably a little off)
5d2 - $2500
50D - $1100
24-70 - $1300
100 L Macro - $1000
Tamron 10-17 fish - $400 used
35L 1.4 - $1400
580EX x2 - $800
~$500 would be consumed by triggers, CF, rechargeable batteries, bags, and other little gadgets.
The remaining $1,000 would get me registered as an LLC, buy insurance, a website and on-line gallery, a couple of low-cost software applications. Ideally something is left for marketing, but if not, there's always CL and local networking.
As a matter of personal choice, I do not believe in loans. No credit card debt, I pay cash for my cars and have only a small mortgage left; that's just the way I am. If I had to, I'd work a bit under-equipped in that sub$1k range and 100% of my revenue would be reinvested in gear until I achieved at least what you see above. Hopefully by then, I've gathered enough portfolio and experience to advance price, begin to get more sophisticated about marketing, etc.