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Hey Lino,
This is a little peculiar. Where is all the good advice?
My $0.02 US (approx. $0.0275 Can) would be that Mercedes will charge you a premium. If a tranny rebuild will fail, most likely it will be within the first few months... If I were going for a rebuild... I would go for the "Mercedes specialist" (Option#2) and save a few Dollars. As long as your satisfied they are honest and capable. You are getting the same deal as far as you can determine.
The used tranny option is also something I would consider, especially if the 300E trannys will work in you car as you have suggested. I think I would look for a low mileage wreck and try to use some parts off of it to help foot the bill and keep as spares for your self... Though, that has been MY focus since I failed to procure a $300.00 front end wrecked 87 300E before Christmas.
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