I'd pay $20k tops for a super mint low mileage 1999. Any more and I'd go W220 shopping.

$10k-$15k will do good examples.

$10k and under for dogs.

I wouldn't buy a W140 made before 1997. I want the 722.6 trans and all the updates. If I ever go W140 I think a 1999 S320 or a 1999 S500 Grand Edition would be what I would hunt for.

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2006 CL500
2009 C300 4matic
1969 280SE
2023 Ram 1500
2007 Tiara 3200