Welcome to the forum.
I am looking for a daily driver for around $20k-$25k... I live in California, I have no need for 4wd... I quite like 500Es, SL500s, CL500s, S500 coupes, E43AMGs, E320 coupes, 560SL, 450SL, SLCs, short wheel base S classes and coupes.
Since it's on your list, I'll put in a good word for the 560SL (R107 chassis). Excellent car for sunny California, as long as you're not too hung up on fuel efficiency. Even in that area, it's not really all that bad: mine gets 15-17mpg in mixed city and highway driving in the NYC area, which is the same as what my Dad gets in his 3.0L BMW X3.
I bought a one-owner '88 560SL with full service history, no accidents, no rust, and 69k on the clock for around $12,000. Mine has been absolutely, dead reliable after two years and 20k miles as my daily driver.
There are enough out there that you should be able to find a cream puff without any trouble. An '86 model will now be 25 years old and qualify for classic car status, which can make insurance and other issues easier to deal with.
If you're looking for something truly special, don't overlook the 190E 2.3-16
with the twin-cam Cosworth engine and Gruppe A touring car history. Compared to the 560SL, it will be significantly more difficult to find one in pristine shape, but it's worth the search. Incredibly rewarding to drive, and (like the 500E) it's a real sleeper. People have just started discovering the 16v again now that the supply of good E30 M3's has completely dried up. Demand has started to increase. It's a future classic.