SSL for multisite

I need to install an SSL, but I have never done this and don't fully understand the process and what to expect. I will be using pro sites and new blog templates to allow users to subscribe and get their own site. Here is my thinking of how I am going to go about doing this. What are the errors in my thinking?

1) Get a dedicated server through HostGator

2) Have a comodo wildcard ssl installed by hostgator to wildcard subdomain, *.mydomain.com.

3) Using pro sites and new blog templates, I would like clients to sign up and get a new site with an SSL automatically installed on their site as soon as they get their site.

What problems am I going to run into and is this an oversimplified expectation of how the process should work?

Support at hostgator is telling me that SSLs won't be created using a wildcard symbol (*). On their support page, there is this paragraph:

"Each time you wish to have an additional subdomain load securely with https, the virtual host entries for the subdomain need to be added manually by our administrators. This is true even for new subdomains created through cPanel. Anytime you would like a new subdomain to load securely with the wildcard SSL, a re-issue request via phone or Live Chat will be necessary in order for it to work correctly."

Is this a limitation of hostgator and/or comodo, or a limitation of all certificate authorities and/or all hosting providers? What is the solution to make this more automated and less dependent on their system of installing ssls?

Hostgator support also told me that "massive configuration will be needed to have my SSLs working" Is that true? Or do the plug-ins offered by wpmu dev take care of all of that? What are they talking about?

Is there a simpler, more automated way to do what I'm trying to do?