I've done that kind of stuff and, against an advanced opponent, you tend to lose. (Although you can roll the average webmaster)
Remember that IP addresses have a market price of about $3 /month, and that's what an honest proxy cost Honest proxy providers rent machines in data centers and have them bind to a wide range of addresses, all in the same netblock. If you're coming from 20 different addresses in a netblock (paying $60) a month, you still look suspicious. These guys might have machines in several data centers, but they can't put you into hundreds of different netblocks.
The economics might get better if you're sharing the proxies with other people, but those other people are up to the Devil's work, and are busting their asses 24-7 getting the IP addresses in everybody's block lists.
As for Tor, quite a few organizations block or limit Tor traffic... Databases of active Tor gateways are available, and sites like Wikipedia use them... Wikipedia won't let you make anonymous edits from Tor, because they don't like dealing with griefers who use Tor.
Now, some people will use hacked machines as proxy servers. A botnet can create a nearly indetectable cloud of IP addresses, but as far as I'm concerned, use of a botnet is an ethical line I won't cross.