1. In order to provision my site for SSL, I have to upgrade my PowerDNN subscription from Personal ($20/month) to Professional ($50/month).

Yes this is true.

2. SSL Certificates are only valid for TLD domain names and they cannot be aliases.

Yes, that’s true, SSL certs are unique to a domain. You can purchase a “wildcard cert” that is valid for all subdomains. For example, you could use a wildcard cert for both these domains www.smith-consulting.com and store.smith-consulting.com. Wildcard certs are usually a bit more expensive though.

3. Reading the DNN Registration Pro Manual…I can’t figure out one thing:

a. To make SSL happy, I believe I have to place all the eCommerce pages (for all the alias sites) on www.simply-publishing.com.
You could have ecommerce pages on each of your unique domains if you purchase an SSL cert for each domain then install the registration pro module on each portal domain.

b. So…if someone clicks a “Buy Now” button on a sub-site…and gets linked to a DNN Registration Pro-powered eCommerce page on the main site (www.simply-publishing.com) …and Registration Pro does it’s magic with Authorize.Net…and, assuming the transaction comes back from Authorize.Net as ‘approved’…then…I’m stuck. How do I configure Registration Pro to set permissions for a User and a Role on an aliased sub-site (for example: www.myplanonapage.com)?

The portal that you install the dotnetnuke registration pro module is the portal where the user’s role will be added or removed. You can configured the module to redirect to a different portal/page after registration but there is no way around the role issue. The solution is to install the registration module on each portal the you have unique domain names for however you will have to buy a cert for each domain.

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At your service,
Dave Smith