My wife had a '97 328ic. If she had bought it new (we could assume no used car problems) and it had a warranty for a problems that would likely pop up, I would highly recommend the car. It looks great, was comfortable to drive, was great with the top down, handles well, and that 2.8L straight 6 is a great little power plant even with the automatic. It isn't the M3 3.2L but it kept me entertained. My mom's '99 323ic (2.5L but choked with a horrible exhaust) is a big step down. I think the E36 automatic is pretty darn good...but I guess I've never paid too close attention.
All that said, I was jumping for joy when she sold it to buy a Toyota Rav 4. I spent almost as much time on that 328ic as I did on my 3 other cars. On top of the E36 common problems ie. faulty brake light failure message, HVAC resistor cold solder joint, passenger side seat belt tentioner, and bushings the convertible add a supremely complicated power folding top with a maze of strings, bungy straps and crappy plastic loops. The top had constant folding problems and the "wings" for the headliner would constrantly break and the flaps would be blowing in the wind.
By the end I figured out how to fix all the problems that ever came up, and we sold it in great shape, but I was always asked to fix something. Normal used car issues? Maybe, but this car was bought with 50k miles and sold with 90k so it wasn't a 150k+ example. We never had a single engine, transmission, brake or body problem or anything else that would leave you stranded, but it was a lot of small nagging problems.
So I'm going to sum it up and say you'll likely have a lot of little issues, but every time you drive the car you will be happy you have it (as long as you're not starring at a warning light! :)
