The cost starts at a few grand for the parts and moves up to a few grand more with labor, and it's a picky job that offers ample opportunity for a simple error to destroy the new transmission. In other words, if this would be your first transmission swap, it shouldn't be.
Buying a donor car guarantees you not one more mile of use before transmission failure. If you love your car (and we here all understand that feeling) then you need to assess your long-term goal for it and your cash flow in the meantime. If you love the D2 in general but don't have a particular attachment to your current example, I would suggest finding the cleanest, best-maintained example you can find with a known bad transmission, and plan to replace it upon purchase. Your friend's S8 sounds like it fits the bill, not too many 03s out there and far less in good shape. Regardless, don't talk yourself into believing there is a scenario in which you own a D2 A8 for any real period of time without purchasing a transmission or having yours rebuilt. Your car sounds like it needs an awful lot of work to be in great shape, so if you can sell it to fund the purchase of a new one and put the money you were thinking of spending on the car in the link you provided here towards the transmission, that's a solid move.
~Sam
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