I hate to say this, but I've heard from a few local BMW Car Club members who own one like yours mention that the automatic transmissions on these are notoriously weak...
Good luck, Doog. I've always loved the E39, and I think a 530i with those sport wheels have looked fantastic. I would love to see you getting this back on the road and enjoying this car.
In all the research, owner reviews and forum lurking I did, I never noticed any comments on the 530i's gearbox, but then again Bimmerfest's E39 section has a higher percentage of 540i owners compared to any other trim level. Most of those who have 530is have the manual, so I can see why I didn't hear much about the autobox's longevity. I'm feeling two main issues right now, but both seem to go away once the car's warmed up. At a stop, I feel this sort of odd vibration, thudding feeling, which our mechanic told me was the torque converter. When I shift into from park into reverse, there's a slight delay, followed by a very noticeable lurch as it gets into gear. Odd stuff, I must say.
My mom was very impressed with the car when she saw it for the first time and decided that a mechanical inspection wouldn't be needed, which we've now learned was a costly mistake. If she'd known of the problems, there wouldn't be a 530i in the driveway, or rather the mechanic's driveway now, as it awaits repairs tomorrow. If I heard that the car would need work after she looked at it, I would've said no as well. That said, if the car were to be sold, I'd regret it immensely. The car's so nice cosmetically, and the driving experience is so satisfyingly precise. Luckily, the Bimmer's not going anywhere. The torque converter issue will be dealt with when it becomes a bigger issue. Other than that, I'm attached to the car, even with its unexpected issues. Not being able to drive it is slightly torturous, but it's better than whatever bland Corolla I would've been given if I wasn't a car enthusiast.