What do you think of this method of "list building" and "sales funnel"?

Ok before I pull out my wallet and actually start to SPEND MONEY...Considering that I am inexperienced in IM, I want to make sure that my overall plan is a good one before I actually pull my wallet out and spend money on driving traffic/outsourcing....

I have 6 eBooks, which I intend to sell as a "package deal" or maybe even label it as a "course"

The overall message of the package is how I have personally constructed my lifestyle in which I have become a full-time, paid musician. I used to work full-time as a mechanical engineer, and I did that for 7 years. Music used to be nothing more than just a hobby for me. However in May 2012, I quit my job in the pursuit of self-employment so that I could have more time to focus on my true passion in life (music). However, simply playing music alone does not provide me enough money to cover all of my expenses, and therefore I needed to develop a "multiple income stream" mindset rather than just simply relying on a paycheck (which requires me to work an uninspiring, full-time job).

My 6 eBooks are all geared towards that one overall theme. One of them in particular explains how I make a decent monthly income from reselling items on eBay.

I'm considering taking the following steps:

1.) Purchase Optimizepress core package for $97, which allows me to use Optimizepress on 3 sites total.

2.) Create a subdomain for mywebsite for which will be my initial "landing page" - landingpage.mywebsite.com.

3.) On this landing page, it will be a nice sales copy that provides a great deal of information about what is included in this "package deal". I will start out with explaining "my problem" (I wasn't passionate about what I was doing), and I will then explain how I went about solving my problem (quitting my job and figuring out how to create this new awesome lifestyle, while still being able to afford my mortgage).

4.) In addition to pointing out the titles of each of the books that are included in the package, I will go into a bit of excessive detail about the book on eBay. I'm even considering including a video about how I do my eBay thing. I will also go into good detail about what each of the other books are about as well too.

5.) At the bottom, where the "take action" button is. I will have a form for where they enter their email address in order to get the first book free, which is an 85-page PDF document... It'a a pretty nice "freebie" too, because it's actually a full-length book as opposed to just a "Free report" or something. I will make no money from giving this book away, but it will enter them onto my mailing list.

6.) From there, I will have a series of follow-up emails set-up in my aWeber account:

- Immediately after they confirm their email address in order to receive their one book for free, I will give them the opportunity to purchase the entire package of six books for the price of $27. Also, included in this offer will be an opportunity to purchase any of the books individually as well.

- An auto-generated follow-up email 3 days later providing a nice article which serves to provide free value. Additionally, I will "soft sell" the full package and the eBay book in the footer of the email

- An auto-generated follow-up email 6 days later providing another nice article, with the same soft sell.

- An auto-generated follow-up email 14 days later with another nice article that, and again the same soft sell in the footer of the email.

NOW...This is the point where I start to get confused:

7.) After they have been on my list for 2 weeks, they will be part of my weekly broadcast which will either be a new blog post or an affiliate offer. I'm not quite sure what to do here.

-Do I keep mailing them on a weekly basis, always with the footer of my email displaying my products?
- Do I simply just keep sending them new blog posts on a weekly basis in order to "keep in touch" with them?
- How would I pitch affiliate offers to these people?
- How do I separate the people that freshly sign up to my list from those who have been on it for awhile and are receiving my "weekly updates"?

8.) In order to drive people to my initial "landing page", which serves as a sales copy/opt-in page, I will use a form of paid traffic. I'm not quite sure which type I will use yet. First, I need to design the sales page, and the follow-up email series, and make sure that the whole system is in proper functioning order before I pay to drive traffic to the initial landing page.


Ok, so that seems like a reasonable way to build a list and potentially sell my eBooks individually or as a package.

However, I'm not going to lie...I am nervous about spending money on something that I'm not quite sure about. I'm asking EXPERIENCED list builders for a critique on this plan.

Thanks!!