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How Hard would it be and where do I start
 

I would like to set up a few sites, selling intellectual property. I would like to add something like a CS-Cart but that would allow for a instant digital delivery. The other I would like to have a subscription service.

I would like to maintain and manage all content on these sites myself.

The question is
How would I find a subscription service with a monthly billing system that kicks off non paying users.

Where do I find a shopping cart with instant digital delivery.

Third and most important question, I have no web developing experience. How long would it take me to develop the skills needed to accomplish this.

Where do I start?
what books, tutorials, classes etc.

i know that E-junkie Shopping Cart for selling downloads & tangible goods offers digital delivery, and its super cheap, cheapest plans are 5$ a month and it easily integrates with google checkout, 2co, clickbank, paypal, and authorize.net

you can also set up a subscription service with them too. they have tons of tutorials for setting everything up, im a newbe in all of this too and this one was really really easy.

try googling around for more info, or just look around e-junkies site

thanks a lot!

In regards to web developing skills, i recommend books from SITEPOINT (google it)