This is only a solution for the crappy updates that wipe your progress.
I recently replaced my 2 xboxes with new ones in the middle of going for this achievement so I didnt bother to transfer my player data for the online achievements, however, my wife did.
I thought of an idea which was to log in with a silver account (or gold if you want) to trigger the update. Let the game update then sign out and sign in with your main account.
I can confirm this method works as my wife has her record, so you can carry on from where you left off regardless of any updates due to your cache wiping or whatever