Hi Daniel. Agreed that the results should be similar in your Rocket Player live list and iTunes smart playlist, though they might not be identical. iSyncr is supposed to be compatible with iTunes, but Rocket Player is a general-purpose media player, so it may have a slightly different approach to date calculations. For instance, does 30 months mean 30 x 30 = 900 days? 30 x 31 = 930 days? Etc. But the difference should be small.
I tested your scenario on my phone. I created a smart playlist in iTunes with 2 rules:
"Last Played / is not in the last / 30 months"
"Media Kind / is / Music" (to exclude videos, podcasts, etc.)
I checked "Match only checked items" (because I don't sync unchecked songs with iSyncr) and "Live updating."
Then I created a Rocket Player live list with 2 rules:
"Last Played / older than / 30 months"
"Folders / contains / syncr" (to make sure only songs synced by iSyncr were included)
I checked "Rule Required" on both rules and set the list limit to 50,000.
The iTunes smart playlist returned 22,126 tracks. The Rocket Player live list returned 21,680 tracks. The difference of 446 tracks is only 2% of the list total, so I assume it's just due to calculation differences.
How many songs are showing up on your Rocket Player live list? If it's a small number, it could be due to calculation differences. But if you're seeing radically different numbers of songs, here are some ideas:
1. Make sure your Rocket Player live list is only including songs from your iSyncr folder. You can add a "Folders" rule to the list that specifies a folder name. My iSyncr folder is named "syncr," which I think is the default. Also make sure to check "Rule Required" on both rules in your live list. Does that change the results?
2. Make sure your iTunes smart playlist is updating. Right-click on the list in iTunes, go to Edit Playlist, and make sure "Live updating" is checked. If you do sync unchecked songs with iSyncr, then make sure "Match only checked items" is unchecked. Does the iTunes list return tracks now?
3. In your iTunes library, go to the main music view and sort by the Last Played column. How many songs have a last played date that is either blank or older than 30 months? Is it roughly the same as what you're seeing in Rocket Player?
4. Spot check the dates of a few songs showing up on your Rocket Player live list. Long-press a song on the list, select Get Info, and scroll down to Last Played. Is the date older than 30 months? (This includes songs where the last played date is blank.) Compare this date with the last played date for the song in iTunes. Are they the same? If they are not the same, it suggests an issue with the iSyncr sync--the metadata for your songs didn't transfer correctly. Did the other metadata for the songs, like artist/title/genre, transfer correctly? If the dates are the same, it suggests an issue with Rocket Player itself.
P.S. I'm an iSyncr/Rocket Player user, not an employee. These are just my inexpert suggestions. But I'd be interested to see what results you get!