Is there a legal basis to challenge them on this? Free speech? Right to assembly?

I'm not lawyer, but they've clearly earned themselves a lawsuit.

i'd like to see what his take on this whole "tax email to reduce spam" scheme is, even though i can guess what he thinks.

If you live in Houston or the surrounding southwest Texas area, and Time-Warner is your cable provider, you lost cspan2 and cspan3 months ago.  

The lies TW puts out are amazing.  First they said that cspan wanted to go to digital-pay-to-view.  Cspan said that was not the case (cspan, being cspan, does not call people liars), and they wanted to stay/get back on cable in Houston.

Then TW said they needed the channels for pay-per-view bandwidth.  But to this day, the old cspan2 channel is snowy-blank.

Bottom line, Time-Warner has censored the only outlet in Houston for unbiased, uncensored, unspun, commentary-less news.  In the meantime, none of the Fox Fascist Propaganda channels has been touched.  Coincidence?  (Probably.)

Add Time-Warner to your list of right-wing fascist  broadcast companies bent on turning the electronic landscape into a vast right-wing wasteland.

...my GF is a TTY rep and she said that when she fields calls from customers who want to cancel, AOL says "we want to keep you as our customer, here's 3 free months!" and don't actually cancel the account. They repeat this ad nausem as long as the customer calls every 3 months.

Forget to call and you get charged again.

I think we need some serioues direct action against AOL.

 In the real world, this would be called Protection money.  You can't trust the cops, we will take control of the bad guys as long as you pay us to protect you.

 Cyberspace:  We have these spam filters that don't always work properly.  If we verify you as legitimate, for a fee, we will make sure the spam filter malfunctions will not hamper your emails to our customers.

Free speech, as defined in the First Amendment, means that the gov't does not have any say in private speech, pro or con. AOL is entirely within their rights on this, and in fact are protected by the First Amendment: private speech, private company, consenting customers.

Now, if the practice pisses you off, great, take your business elsewhere. But the simple fact is, this is no more dangerous than Fedex. It's a premium delivery service, that's all. Fedex's existence does not help or hurt regular mail and the Goodmail system won't help or hurt regular email. Senders and recipients of Fedex generally seem satisfied, no?

If you really believe it, make a specific prediction and we'll check it in a couple of years. Are you predicting that AOL's spam filters will show an increase in false positives? Give us a metric.

Regarding AOL's motives, "control" but not profit? How strange. More here.

I know this deals more with the internet backbone than AOL services, but do consumers still actually play AOL for their shitty ISP service?

Back in the dial up days, even when there was competition, they were terrible with constant disconnects and busy dial in servers.