Why is the podcast validating correctly but getting rejected by iTunes

You cannot get iTunes to stop doing this, sadly, and I don't think you can exactly re-implement the Doug's Applescripts solution for expired playlists for Windows - it relies on manually updating each podcast rather than calling update all. And the iTunes COM object does not seem to expose a way to update individual podcasts, only the entire list.

And I am 99% certain that Matthew is incorrect and that refreshing all is not sufficient to bypass the recently listened count. The wperry link will mark the podcast as listened to, which is the same issue as your workaround that you find unacceptable.

I do think, however, that you can workaround this issue by right-clicking and choosing refresh. While that's unnecessary to actually get new episodes when you have periodic updates set, it will reset the clock, as it were, and prevent it from stopping when you don't listen for a while. Whether this is actually any better than just dealing with it as it comes up, however, I don't know.

I'm not much of an AppleScripter, so this is modified from some scripts at Doug's AppleScripts website, but it's GPLed, so derivative works are allowed as long as they're also GPLed.

My idea was to make a script that could take the release date, which can't be used in smart playlists, and store it in the last skipped date, which can be used in smart playlists. If you just want to do this for podcasts (not for songs, for which you might actually use the last skipped field), just select your podcasts before running this script.

Once you do that, you can create a smart playlist selected on the "Last skipped" field to get the recently released podcasts.

So here we go:

 (*
 You can rename this script to whatever you want
 but please keep this information intact. Thanks.

 This program is free software released "as-is"; you can redistribute it and/or modify it under the terms of the GNU General Public License as published by the Free Software Foundation; either version 2 of the License, or (at your option) any later version.

 This program is distributed in the hope that it will be useful, but WITHOUT ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the GNU General Public License for more details.

 Get a copy of the GNU General Public License by writing to the Free Software Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.

 or visit http://www.gnu.org/copyleft/gpl.html

 *)

 tell application "iTunes"
set sel to selection
if sel is not {} then
    set ofi to fixed indexing
    set fixed indexing to true
    repeat with thisTrack in sel
        set reld to release date of thisTrack
        tell thisTrack to set skipped date to reld
    end repeat
    set fixed indexing to ofi
else
    display dialog return & "Select some tracks first..." buttons {"Cancel"} default button 1 with icon 0 giving up after 15
    return
end if -- no sel    
 end tell