My best guess for this would be an HL.exe error itself, try to start the program then check task manager and make sure the status on it is setup right, if this doesn't help and it seems normal, when your on the main loaded screen input the following commands...
'developer 1'
'fps_max 999'
'net_graph 3'
'net_graphpos 2'
Watch the FPS, and if the FPS locks up a lot in the game then it's probably GFX related. If the FPS isn't locking up and it's randomly crashing I can only assume that it's a Steam issue, then I would delete 'clientregistry.blob' restart it, no luck there then just fully reinstall Steam, if the problem persists, PM me!
You can also delete the 'cstrike' folder under your username steam files, delete the following folders and let it reinstall...
'cstrike'
'valve'
can you put screen shots or any image to let us understand your problem as well !!!
Gl