The migration went pretty smooth all things considered. There were a few complications but nothing significant. I think the largest issue was that my site was already behind CloudFlare so I had to bring all things back to Godaddy before the migration could happen. I gave the SiteGround team access to the server via SFTP and they got everything migrated promptly. There were several email exchanges with the technical team and each took about 45 minutes for a response. Overall I was happy with their customer service and technical support.
In the end things didn’t pan out with the self-signed SSL certificate. So there was the SiteGround Migration and My Return to Godaddy. Once I was into my SiteGround account I realized that there are all sorts of add-on (paid) options for this and that. The pre-sales representative was correct in that they will install a self-signed SSL certificate, however there are several non-trivial fees to do so. After this discussion I felt as though I would continue to run into issues that would end up nickel and diming me to the point of dissatisfaction so I ultimately decided to head back to Godaddy where my account is prepaid for a while.
The SiteGround representative I chatted with while cancelling was also easy to work with. He seemed to understand my concern and offered a discount to get me up and running with the self-signed certificate, but I had already made up my mind. They promptly closed my account and I just pointed all DNS records back to Godaddy. Within a few minutes we were back online; no harm no foul.
I’ve come to the conclusion that these managed services just won’t cut it for me. They are designed for non-technical folks who simply cannot do these things on their own. I’ve decided to roll my own server in aws in order to have full control end-to-end. No more non-sense with managed services.