[masraum]

If it was me, I'd hang on to the '89 like my life depended on it.

But, it really depends upon what you want the car for and use it for. Is it a fun weekend driver, a daily driver, a show car, track star, etc....

Back in the day, I daily drove an '88 911 targa. If it's in good enough shape, that's an option, but with the appreciation that those cars have seen that might be a bit scarier to do. And a 997 would likely be a more comfortable driver with more creature comforts.

If it's a weekend fun car, definitely, I would think hang on to the 997. But it's an entirely subjective thing. Drive a few 997 and see what you think and feel after driving them. How much do you drive the '89? A lot, a little, do you find you don't drive it as much as you think you should? Do you love the driving experience?