Just my own 2˘ after owning a Euro-Market 107 for over 20 years: If you rely on a mechanic to work on your car, stick with a US model. The 280s will be Euro market or "Grey" imports. Service information and parts procurement can be difficult at times.

The Automatic is fine if you have it tuned properly. If they're wrong, they're just a DOG. Be aware of the timing chain issues with the early 380s, the US market cars had a single-row chain that wore prematurely and can be expensive to maintain or upgrade to the double-row chain. If you want a 380, hold out for one with a double-row chain and proof that the guides and oilers have been done recently.

If you want a well-documented and more DIY-friendly V8 car, look for a 560SL. Depending on how heavy your foot is, fuel economy can be similar to the 280.

Just ramblings from someone with a love/hate relationship with the 107!

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Current stable:
1995 E320 149K (Nancy)
1983 500SL 120K (SLoL)

Black Sheep:
1985 524TD 167K (TotalDumpster™)

Gone but not forgotten:
1986 300SDL (RIP)
1991 350SD
1991 560SEL
1990 560SEL
1986 500SEL Euro (Rusted to nothing at 47K!)