And if you do pay the $60, you can only manage a single legal entity. Which means, if you are the certificate manager of some organization, you can either get certificates in the name of that organizationation (after completing the paperwork and paying the additional $60), or for your own private sites, but not for both at once. Yes, after completing the paperwork for getting certificates for your organization, you lose the right to get certificates for yourself. Crazy, but true!
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?
Oddly enough, if you don't pay anything at all ("class 1 certificates"), you can get certificates for several associations and yourself at once. Of course, then you can't get wildcards or SAN certificates, so you are forced to use SNI (more hassle to set up, and might not work with exotic browsers).
Technically, yes, but policy-wise, no: Class 1 certs are not intended for commercial use.
Wow, a place where beer is even more expensive than here in Luxembourg! But seriously, I guess the $9/year is for plain certificates, no wildcard and non SAN? In that case it would compete with StartSSL's free offering, rather than their $60 plan. If it actually does include wildcard certificates, I would be interested in details.
It's hard to directly compare the two offerings, as StartSSL charges for validation but you can issue numerous certificates at no additional cost. Other CAs charge on a per-cert basis.
As you suspected, the $9 offering from PositiveSSL is for a single, non-wildcard, non-SAN certificate. NameCheap also sells Comodo PositiveSSL multi-domain certs for $30/year for up to 100 domains, which is quite a reasonable price. Of course, those certs are domain-validated only. Organization-validated multi-domain certs start at $90/year. That's cheaper than StartSSL, but only gets you a single cert with multiple SANs. If you needed more than one, StartSSL is the more economical choice. Wildcard certs are also available, with Comodo wildcards costing $94/year.