Tor relies on various kinds of diversity to protect anonymity. Your proposal probably reduces diversity in terms of sysadmin, hoster, network and jurisdiction.
I interpret his message differently, namely the "we" I see as referring to the community as a whole. It's not that dirt-cheap that any individual could host 1000 servers anyway, even at only $5 a month that would be $60k a year, which I doubt many individuals are going to not care about.