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I think it probably depends on the lender and how the new TL is reported. Does the new lender report the entire history of the loan, or just from the time that they took it over?
If the new lender is reporting the entire history of the loan (from the date it was originally opened with the old lender) then I think you should be able to get the old TLs removed. That's the case with one of my loans, and I'm disputing the old TLs - because the history of the loan is being reported twice. The new lender will not budge on reporting the info from when the old lender held the loan - they told me to take it up with the old lender or dispute the old TLs.
I would try GW letters to the original lender, if you haven't already. If you have tried that with no success, just keep at it. As a lot of people here have experienced, it only takes one yes to get something removed - and sometimes that yes comes after 20 no's!
My issue is that both the new and old lenders are reporting the five years that the original lender owned it, which includes one 30-day late payment. I wrote to the new lender about it and they say they're reporting correctly, which is fine - I probably did pay late. I'm debating whether it's worth it to dispute the original TL, though - while it would probably be successful, I doubt that one 30-day late almost six years ago is making any difference to my score. It's the only negative item on my CR, though, so it bothers me that it's reported more than once.