I've become somewhat partial to 97 C280 / C230 and to a lesser extent E320 ( not so much up for the front end / headlights )

96 - 97 was first year for 722.6 electronic shift trans ( also used in Chrysler products, many trans shops can rebuild them Vs not so much with the older 722.3 / .4 / .5 )

97 was the last year for a mechanical key, later cars got a somewhat problematic key fob / electronic column lock. 97 was also the last year for the M104 inline 6, 98 brought on a somewhat problematic V6 that later got better. ( crank pulley issues for sure, from what I recall valve cover breather / EGR carbon issues. )

The C and E can have rust issues so stay out of the salt / snow belt.

Both of these cars are built to a price but are decent cars. I got the 97 C280 for Mom to dive and I'd pick it over my SL for buzzing around town.

I'd think a really nice 97 C or E could be had for 5K easy.