I sort of cheat. I quite easily say 200+ but..........
I am in Canada, thus I have most .ca and .com of the domains. So like using reddit as an example, reddit.com and reddit.ca. To most I have both .org and .net as well. Three redirect to .com. I also have many who are domain hacks.Using delicious as example...I have del.icio.us and delicious.com. As well as delicious .ca/.net/.org
2000ish