Exhaust was replaced (sounded very cool before it was fixed).
Some new tires and alignment.
Steering wheel started to come loose, was tightened, wasn't cheap.
Starter was replaced (solenoid gone bad).
Rear window mechanism isn't made very well, mine has scratched the window and has rendered the rear defrost useless.
The more aggressively you drive it, the more oil it will leak and burn, however it does stay pretty moderate (one quart every 2 weeks approx).
Serious lack of power from a 5.0 engine, the 307 apparently has the worst power per displacement ratings of all time.
It loves gasoline (14mpg when in need of a tune up)!!
Supposedly the transmissions have some issues with wandering in overdrive.
Very enjoyable ride, I would highly recommend this car for trips or to float down the road in wooden style. Power seats work well and the bench is very comfortable. steering feels detached (you can maneuver the wheel with your knee easily). Great for carrying lots of friends. careful parking this car, its very large. Very dependable. If possessing wooden qualities, this car will enhance your image significantly.
I don't know what you're used to driving, but the 305 is very quick on acceleration in these cars. I drive somewhat aggressively and don't have any issues with the motor. It was used in many other cars through the 80's so it was more than suited to these cars. I find the engine to be perfectly adequate. The V6 is the underpowered motor.
The 305 and the 307 are both 5.0 liter V8 engines, but the 305 is much more powerful.
I have never had a Caprice wagon, but I understand they all had 307's. I have however had several Caprice sedans with 305s, as well as several Olds Delta 88s with 307s, and in my experience the 307 is much smoother and more durable. The power difference was too small for me to notice.