No disrespect taken, reality check is what I'm after.
I value all your opinions, knowing you guys are guessing at my financial status. I have a good job, with no debt and good work prospects for the next couple of years. I should save money insuring two cars rather than three, and the remaining 300D would be a rock solid reliable transport should the newer Benz decide to become a shop queen on me. You have the experience with these cars not me. I'm used to the old ones, as you can see. They seem so much more reliable just because of their simplicity. And shop costs are lower cause of the ease of working on them.
So, I should budget 2 to 3 grand in the first year for maintenance? (Worst Case Scenario)

It doesn't seem like the price is that high for a $4,000 car that was 40,000 when new, only 10 years ago. That seems like quite a depreciation. Market saturation would be my guess in this area.
I wish I knew what the maintenance costs would be. Any of you guys have a few examples of repair bills with 300E's? Date of repair (to show frequency), amount and brief description would be awesome.
I have a humble amount of DIY potential too.
Thanks in advance, (understandable if you're too busy)

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63 220S W111
76 300D W115
2013 VW JSW TDI M6

previously-
73 280 SEL 4.5
86 300E 5 speed
2010 VW Jetta TDI M6