The HBO HD options are weak right now, but there was an annoucement a few months back that stated HBO would have all channels in HD and that DirecTV would be carrying it. You would be looking to get the PLUS HD/DVR package at $69.99 plus HBO at $13.00 for a total of $82.99/month. If you went premier, it would be $99.99 plus $10 for HD, plus $5 for DVR for a total of $114/month. You'll also have another $5 for each additional reciever.
Personally, I go with the Premier because of the HD premiums (Starz, Showtime, Movie Channel, HBO, Cinemax) and skip on renting DVDs. The extra $30 is worth it.
I am very satisfied with the PQ in HD, there is still a lingering issue with lip sync. I can't comment on which is better as I've not seen a Dish HD signal since they went to MPEG4. All I can say is, I'm very picky and with DirecTV, I am very satisfied.
The HR20 series has made tremendous strides in the last year. The On-Demand stuff is working well (requires a high speed internet connection and an HR20). Remote scheduling is working on my account and will be available to everyone soon. I'm also able to play music and photos from my computer along with a few video files (not all...yet..).
I enjoyed having the Superstations, but it is something I've done without and not missed for over 2 years. I really liked them for baseball, but as teams moved off of the supers, that advantage disappeared. It was...Dodgers, Yankees, Mets, Red Sox and Rockies games, now, you only get a few Mets games.