Best approach to buying tools?

Personally I'd get a Craftsman set when they go on sale and then scour craigslist. You can find tons and tons of old school quality tools for cheap on CL. I'd much rather have an old school pair of used Klein cutters than some shiny new brand that hasn't made their name in the cutting business.

Certain things at Harbor Freight work fine and certain things are hot garbage. Always check the reviews on their site and google the tool to see what other people on other forums are saying about it. One tool might break as if it was made for a 5 year old and the next tool might work perfectly and save you $50. Do your research.