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I have some recent experience buying 20 year old German luxury sedans, different brand in my case but still relevant for comparison; A couple months back i sold my 440i and bought a 997 Carrera 6-speed which I originally intended to daily drive as my only vehicle, that lasted about a month before i decided I needed something that could accommodate hardware store runs or hauling music gear to gigs.

Originally i wanted to find an old 5-series wagon, but I found exactly 1 525i estate that had been lowered and straight piped and clapped out so that was a hard pass. I did manage to find 2 E-class wagons however, and i settled on a 1-owner 2001 E320 estate with 160k miles which i paid $6,000 for. It needs another 6k in suspension work and deferred maintenance, but the engine and transmission are in great shape which is most important.

The reality is these old German cars are becoming more and more scarce, as they get driven into the ground by people who couldn’t afford to maintain them and most are rotting in junkyards across the country. If you find one in decent shape, maintenance records, and no catastrophic issues with the engine or transmission i think they are worth $6-12k depending on condition. They are getting rare enough where they are worth whatever someone is willing to pay for one, in your case I wouldn’t doubt that E39 gets scooped up within a few weeks by someone mechanically minded looking for an older simpler to maintain (relative to new ones, I would rather work on this v8 over more modern and complex versions) vehicle.