I know some people have voiced concerns about Gatekeeper in 10.8, but this seems at least as bad. Especially from a normal user's perspective.
The problem with Microsoft's strategy has always been the reliance on companies like VeriSign for whom recurring revenue from certificate renewal is a primary revenue source. And when I've had to deal with VeriSign for code-signing certificates in the past, it's easily cost more than $99 in time ("I'm sorry for the delay, but could you please fax that to us again, only this time, on official company letterhead?").