I don’t want to say this too loudly because I might jinx it, but the gorgeous Mercedes-Benz R107 generation SL roadster is probably near the bottom of its depreciation curve. Prices are cheap, particularly compared to older 60s Benzes with 2-doors but it offers a more sophisticated ride for a bargain price. The R107 was introduced in 1971 and lasted for an incredibly long 18 years of production and was finally replaced in 1989 by the smoother but less cool looking R129, but if you want a deal on a classic, reliable and drivable 2-seat roadster, the R107 is the way to go. Find this 1974 Mercedes-Benz 450 SL offered for $7888 in San Rafael, CA via craigslist.
From the seller:
1974 MERCEDES BENZ 450 SL
cylinders: 8 cylinders
paint color: blue
title status: clean
450 SL. Very good condition. Just had $1,000s spent on maintenance steering and front suspension. Interior and bodywork are in excellent shape. Drives superb. Comes with hard top.
See a better way to drive a classic? firstname.lastname@example.org