"...1, I'm not a huge fan of German long-term quality (or at least my perception of it)..."

Don't repeat the mistakes of those who gave you that impression of Mercedes. Mercedes made but a few 'bad,' cars but eventually some of the brand fell into the hands of 'bad,' owners.

I'd suggest you go toward the upper limit of your allowance, diligently seek an automobile which has all maintenance documents and thoroughly research the particular model before making your selection.

It appears you've already made a fairly good preliminary search and decided on the model which was the best first move. Good luck.

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84 300SD
85 380SE
83 528e
95 318ic