So first of all, SUCCESS! I added NS records for ns1/ns2/ns3.digitalocean.com to my DNS records in Digitalocean, and after a min to propagate the calls to create the certificates succeeded!!! The entire issue all along was the weird DNS setup I have for the domains
And to answer your question, yeah, I'm not the biggest fan of it being split up between Namecheap and DigitalOcean, if I recall correctly I can't use Namecheap because they restrict API access unless you have a certain number of domains or pay extra, and I don't want to lol.
To anyone who finds this issue via Google in the future, make sure you're getting back NS records when looking up the DNS records for your domain, that appears to have been my issue all along!