Changed pfp.
Now that it's clear that AT40 1998-2004 shows are NOT being rebroadcast. I would like to bring up the theoretical benefits Premiere Networks has and what's Dees seems to be lacking in, and it's not just how popular Dees vs. Kasem are. A lot of this is what my opinion and my observations and aren't necessarily fact.
Premiere Networks is owned by iHeartMedia, and shows distributed by Premiere tend to air on many iHeart owned/operated stations. Premiere also has the entire library at their fingertips they can use to air. The distribution of pre-recorded shows seem to be more straightforward to affilates. One thing that can of course hold things back are the limited years to choose from, and they certainly can't air any of the CT40 and it's spinoffs (1989-1998) or Shadoe Stevens AT40 (1988-1995) as apparently those are are with rival Westwood One. AT40 shows have a fiercely loyal, sizeable fanbase and AT40FG, Facebook groups and Twitter are full of people wanting to know what the next shows are going to air or what the new chart is. I definitely don't see this with many other syndicated programming on the radio today.
Dees on the other hand is distributed domestically by Compass Media, so I don't think there's as much links between syndicator and station owners but could be wrong. Based on the stations I could find that air his shows, the kind of affilates that air his retro shows seem to be in smaller markets, load up on a ton of shows and/or the people behind them are music/show/chart junkies. BTW Dees started in '83 but only air '85--89 shows for the 80s block likely due to not having Cashbox chart rights on the '83-'85 shows.
Dees doesn't seem to have a very good archive of old shows, there have been many 80s, 90s and 2K shows they have yet to air while rotating the same shows over again for over a decade. The rotation has gotten even worse in the past 3 years on the terrestrial side airing the exact same shows every year with not even a little bit of mixing like previously. The shows that were distributed to stations via vinyl that are rebroadcast are direct transfers with little to no restoration being done, unlike Premiere does with AT40. Rick's retro shows can often have record skips, CD rip clicking noises, missing segments and other miscellaneous issues.
The file distribution of the shows to seem to be lacking too. An email from an affiliate that was posted on the AT40FG has issues with the Synchronicity and how it pushes out programming. One more thing is that more variety of shows are given on Rick Dees Hit Music App is better than even what stations get. The app offers 80s, 90s, 2K and today's shows commercial free. The retro shows on the app have more variety and can be heard on demand. I feel like any combination of these things I have brought up might be compelling reasons why affiliates might not be fond of airing the Weekly Top 40 and especially it's retro programming even when they choose to air it.