I have a 1990 190E 2.6. I love it. It drives great, very sporty feel because of the heavy front end. My family also has a 1986 190E 2.3 which handles with more agility but much less power.
As far as repairs, there have been few, but when anything serious needs to be done under the hood the space factor is time consuming. The 190 body was originally designed for a 4 cylinder engine (2.3s) and when they released the 2.6 everything became very crowded.
Like all Mercedes, it comes with tons of options and power everything. If you can find one with vinyl interior, go for it, it may sound bad, but all my friends think it's leather and best of all it looks brand new and can withstand all kinds of abusive that ruins leather.
All you need to do to make a 190 current and impressive is replace the stereo with a CD player and you have a stellar small-ish car for well under $10K. Perfect for anyone who parks in tight spaces yet still want a look of class.