I've had a serious love affair with the network beginning with Dream On, The Larry Sanders Show, then moving on to Oz (yeah it was a 'male' soap opera I guess :), Sopranos, 6 Feet Under, Deadwood - which I didn't particularly _love_, but highly respected, and most of all The Wire (best thing to ever grace the screen IMO - they lost $$ on it throughout its run)... and then I killed my cable sub and haven't seen anything of their's since.
Now Mad Men and Breaking Bad are my two favorite shows, they're both on AMC, and I can easily purchase each season on iTunes HD for just north of $30. Every episode is available hours after they originally air. I'd pay twice that much.
Of course, the problem is HBO is just too tightly coupled to big cable. They're one of the main attractions, and as such the kickbacks they get are tied to contracts that prevent them from wresting their content to any great degree. Until this model changes, their A content won't see the light of day, and more draconian measures are likely to be put in place to thwart piracy. It's not HBO itself per-see, but HBO as a proxy for big cable; as a defense mechanism to prop up a flailing business model.