Man thats huge!!

Elance.com is one of the best sites for the freelancers. The other one you might want to try out is Freelancer.com. Don't know about Freelance.com though.

I think some of the renowned freelancing sites are quite reliable sources. However, they are significantly competitive and the often the ppp is disturbingly low. :(

I guess a non-native English writer can be as good as a native in terms of skills and knowledge for writing but as far as the usage the language is concerned, it is really hard to bit a native. It will always come naturally from a native speaker which in most cases is not the case with the non-native writers.

The consistent flow of orders is going to be an issue for sure. But I think if you can get yourself affiliated with one or two larger firms then that part will be covered significantly. They usually invest a lot in promoting their services and thus secures a whole lot of orders from potential clients. So you wont have to worry about getting out looking for clients that often. However, I would say it is safer to have some personal clients on your list as well. But in terms of academic writing, securing a benchmark amount like the one I have mentioned above is going to be quite a challenge. May be you just need to work extra hard during the pick seasons to cover that part.

Avoiding Wikipedia. How about eHow.com and About.com - reliable sources?

I have often received strict instructions from my clients to avoid using Wikipedia for data mining as they consider it as an unreliable source of information. But what about eHow.com and About.com? Can they be considered reliable? Should they be used as resources for Academic works?

As long as you are using double-spaced 12-font size, it should easily hit 275 words a page which is the acceptable standard.

Well I guess if you are making $15 per page and writing about 15 pages a day, it is about $225. Assuming that you are working around 20 days a month, it can easily be $4500 a month and $40,000 annually. But the biggest issue is whether you are being consistent or not. Once you have few regular clients, it shouldn't be that difficult. But the first couple of years will always be difficult for most of the starters.