Several years ago, the BMW E39 caught my eye. And over the years I have owned 3 of them—the $30K was money well spent as I experienced everything this ultimate driving machine, in all its variants, had to give.

As my hunt for early 2000’s M5s on FB marketplace began, I moved my way down to the 540i. I found a 2000 Biarritz Blue 540i with a manual transmission. I quickly drove north to pick it up and drive home.

This was a mid-grade example in a great color, and I quickly racked up miles with it. The sound of the V8 was great, the steering box was awkward at first but easy to get used to and the open diff was amazing. Overall, I enjoyed this car but wanted to move onto a larger daily, so I parted ways and put it back on marketplace. The guy who bought the car had never driven a stick before so for an hour before selling it, I taught him how to drive stick in a large parking lot and he drove it home! Purchased for $6,000, sold for $6,000 – only putting about 8,000 miles on it, since I had a couple other cars at the time, but overall had a blast with the car.

A couple years went by, and I had an urge to buy another E39, but this time I was in a position to find an M5, the hero.

Back to marketplace, I found an Anthracite Grey pre-facelift M5 for just over $20,000. After getting it home from its very detail-oriented-prior-owner, I installed the facelift M steering wheel, put all the trim inside back to its original wood (it was wrapped in carbon fiber) and put back the original shift knob.

With this car back to its original state, I enjoyed every second of it. Now with more power than I previously experienced, an LSD, and ITBs – it was excellent to drive. With this all being said, it is still a very understated car. This was a great road trip car, highway cruiser, did well on backroads, it was a very well-rounded car that lives up to the hype.

After putting 5,000 miles on the car, I decided to take care of the OEM clutch and Flywheel. I had this done at a well-known reputable shop so I could retain paper records of the maintenance.

Since I was going to drop the car off for a week+ and was also prepping a Miata for sale, I needed a car. So, I decided to take the plates from the M5 and Uber an hour to buy a manual (5-speed) Oxford Green over Tan E39 530i. Since I had no other car to drive a new project car is a good idea right? This was a CHEAP example. The car needed A LOT of work (that is enough for an article all on its own!) but I picked up this car for a great deal and drove it home that same night.

Now this was my first E39 BMW with a steering rack…rather than the box. I was very surprised how much more playful and responsive this felt compared to my M5.

So now at this point in time I was able to have a daily 530i for bad weather and more of a weekend/nice day M5. This combo was excellent. And while I went through these cars it inspired a friend of mine to purchase a 528i. This was merely the same as the 530i but with less power. There was no need for me to invest anything into that model, but I did get to try it out.

My big ah-ha moment came later on though, I found myself enjoying the 5 speed 530 more than the M5. I preferred the gearing and steering.

I will tell you this, the only reason I sold both the M5 and 530i later that year was due to someone online reaching out about the M5 and offering me close to $30,000 for it because it was the exact spec he was searching for, and I had a complete set of records for it as well. And of course, the 530i fixer upper was worth market value once I gave it the some much needed attention.

Reflecting on my experiences with the E39 BMW, I ended up preferring the 530i, but I would have only gotten there after owning all three. So, all in all my $30K spent on E39s was that much sweeter knowing that I enjoyed the best of some of the best ultimate driving machines from an era where BMWs were truly driver’s cars that could also be comfortable cruisers.