Never had any issues like these with more modern games, but plenty of issues with older games:
Final DOOM: Distorted graphics, re-installed...nothing changes. Inferior to my DOOM collectors edition to say the least.
CS: Breaks just about every steam update. Broken twice for me now, waiting for a response for support.
Age of Empires II HD: Cursor errors, typing anything in the map editor causes the cursor to vanish. SOMETIMES this fixes itself after minimizing the game. Only just installed this game after buying it in the sale.
Quake II: Refuses to minimize (more of a convenience issue) and crashes frequently if you leave the game after starting it up.
I've not played any older game without some issues.
Before you ask: NO, these issues are NOT my fault: my laptop is very healthy, and I don't have anything disrupting steam etc. I have changed no settings on these games. I have re-installed them all, asked for support and gotten nowhere. All these errors were present the moment I installed them.
I expect issues with older games as any reasonable person would, but is this just poor quality control from steam in regards to checking older games for bugs/errors? Why are they inferior to CD versions?