Will this pricing schema work?

Hi, All. Think I finally have a handle on how to best organize my WPGD layout in using CPTs. Basically, I’m going to have five different CPTs for various “products” then, within each product CPT, I intend on having five different regions around the state. For each, CPT, I’d like to price out the following:

• Free listing via CPT: very limited listing to registered users for free with two images, limited description and phone number
• Enhanced listing via CPT: include more images, social media and website links
• Premier listing via CPT: same as enhanced listing but with the ability to include events – I have an additional question on this per below
• Featured listing via CPT: same as premier listing but includes the featured option

I’ve been looking into S2 Member (I understand Guust is the resident S2 Member expert) and it appears I might need to purchase their Pro level to make use of their one-step registration process as I’d like to keep my members on my site and not keep going back and forth between my site and PayPal. Before I shell out $80 for Pro, I have a few questions:

• For the various CPTs above, would I price them out at “zero” and use S2 Member Pro to handle the pricing and signups via URI restrictions?
• Is it possible create additional CPTs at the event level or only at the places level? If not, I’m assuming I’d only have one events post type much like the places post type and would need to define various categories in it, yes?
• Finally, if I have an “add listing or events” link under each CPT, I’m anticipating having a sign-up form with the S2 Member URI shortcodes for each CPT type. Is this how I should build out the sign up process?

I think I’m very close to having the process mapped out and would appreciate any insight you might provide.

Thanks much, in advance.

Regards,
Kory