Huh. I didn't know that, as I only have ever done the individual verification. It's not uncommon for someone to wear many hats (i.e., to be affiliated with several organizations). It'd certainly be nice if their system allowed for a single individual account to switch between different "identities", so that one could issue certs for themselves or any number of organizations with which they're affiliated and which they've validated with StartSSL.
Have you suggested such an improvement to them?
Yes, of course. They wouldn't budge. Their suggestion: just use the "free" plan instead, there you can wear as many hats as you like (which I did... after this incident they never saw another cent from me). Weird way of promoting your business...
And that's another issue: they don't take any suggestions! For example: some (all?) of their automated mails are formatted as a single long line. I suggested to them that general usage is to stay below 78 characters per line. Should be easy to fix, as they probably use some kind of .txt template, where they could just insert a couple of breaks. Answer: well, at least our mails don't contain a virus (or something equally silly). Hey that's great! But it would be even nicer if the lines were shorter as well. A year afterwards, the issue was still not fixed.
Technically, yes, but policy-wise, no: Class 1 certs are not intended for commercial use.
Well, it's not commercial use, it's for several non-profits and one political party.
As you suspected, the $9 offering from PositiveSSL is for a single, non-wildcard, non-SAN certificate.
Yeah, that's the kind of certificate that you can for free from StartSSL (class 1)
NameCheap also sells Comodo PositiveSSL multi-domain certs [namecheap.com] for $30/year for up to 100 domains, which is quite a reasonable price.
Yeah, that would be reasonable. Can these domains be wildcard, or does each domain only have a single host?
Wildcard certs are also available [namecheap.com], with Comodo wildcards costing $94/year.