I think I figured out my issue. BTW, this is for Ubuntu 16.04.5. I'm doing a virtualbox-iso.
By default, NAT is used for during the provisioning process. I had to change my configuration to reflect a local host instead of the configured static IP. Even the IP obtained when doing ifconfig didn't work.
Ultimately, it's the fact that I'm using root to connect to the new instance. By default, root cannot log into remotely. (PermitRootLogin is set to prohibit-password). I need to figure out a way to enable root during the preseed or something.
The goal is to get a vanilla VM that has a static IP and is accessible remotely by root over SSH. This is what my current VPS provider gives me and there's no way to change the final output for the plan that I have. I have existing Ansible scripts to automate the completion.