Requesting professional advice

I posted this yesterday, I'm posting again in search of more input. Below is an outline of my first full campaign. I basically am looking for professional advice and input on my plan.

I'm currently outsourcing my first ebook creation. I'm paying just under $300 for the job, which comes with .doc and .pdf, TOC, Cover page, and 3d design. (highly rated author at elance)

I plan on building a squeeze page which will offer a free 10 page report. This report will be related to my ebook, but not so much that it takes anything away from it.

I plan on outsourcing 20 to 30 articles to ezine, each covering general issues and solutions for my niche, each linking to my squeeze page via the bio box.

Whoever signs up for my free report will also get access to my site which will basically be a directory of all these articles.

Then I want to offer this ebook to them via email for a cost I've not yet decided. I intend on outsourcing all the SEO and backlinking to my squeezepage and articles. The sales page for the ebook is going to be tough, since I've never written sales copy and I hear that copywriters are expensive.

If this campaign is successful, I want to create a more in depth product to offer my list of buyers. This one may be $10 or $15 higher than the previous, and will focus on a solution to a more serious issue they're having (after I poll them via email).

I've written out this plan after months of research and over a thousand bucks on IM products. I have yet to make any money online, and I figured that's because I get side tracked too easily. I want to perfect this plan once I get professional opinions here on WF, then I'm going to put on the blinders and complete this project.

Thank you for reading and please, be as kind or as harsh as you wish.