Pay to blog and Supporter integration?

On my site I would like new users to sign up for a blog, get 30 days free as a trial period, and then begin paying a monthly fee. Ive found this is all doable with the pay to blog plugin.

My problem is that I would like to also create a "premium package" which they can upgrade to for more money per month. I have come up with two ideas to achieve this. I can set up an "e-commerce upgrade store" as I am calling it where people can purchase custome themes and plugins for a one time fee. I as the admin would then have to manually go into their backend and activate them per blog....or

I can use the supporter plugin on top of pay to blog plugin. and wrap a set of custom plugins and themes into a supporter package. This way I essentially have 2 packages for users.

This is the route I want to go but my problem is that I dont want them to be billed 2 seperate subscription payments (1 for pay to blog and 1 for supporter) I would like them to be charged x amount for pay to blog, and x amount for pay to blog + supporter.

Is it possible to integrate them together when someone becomes a supporter? Does anyone have any suggestions?

Thanks for the help!
Cody