I have a 99 beetle with a bad transmission. Originally wanted to keep her and fix it up. Now thinking it might be better to invest the money in a newer convertible. Any advice? Where would I go to sell the 99 for the best price?
Are you attached to the car in a way that allows for illogical choices in regards to repair?
If so, then fix it.
If not, then don't fix it.
Logically, a car that old is not worth keeping running if it has no meaning other than 4 wheels on the road and an engine to make it go. Not when faced with a repair that will cost thousands.
My 98 is slowly draining my will to live with its constant needs, I highly recommend you don't let your 99 do the same to you if you can.
I would never get another Beetle, or even any other VW, and I'd recommend you don't either. Double that for a VW convertible. That's just more expensive parts that can break and leave you with a bill you don't want.