What to buy

Had to sell my trusty '87 300D about two years ago so my wife could get her "dream car". Well, that turned into a nightmare and she's been
driving 'my' car. So, the dreamer is going (since it's been a hangar queen if you get my drift). Soooooo,
If I had a budget of about $10,000-$12,000 what would be best? Here all Ireally need is room for 5 of which 2 are car seats (the 300D was fine is thiis respect), reliability and decent mileage.
I was thinkin of a newer than '87 300D again or perhaps a TD, although it looks like somewhere in the 90's diesels got spotty.
What are good and bad years, models and engines? I live in northern California where it is flat and mild except for hot summers.
Thanks in advance. You have all been very helpful in the past.

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