Because I love tools, my tool buying philosophy is...
Don't buy it till you need it (your bank account will thank you) And when you do buy it, don't skimp. Tools are one of the few things anymore where the price actually reflects the quality (to a certain extent.) Good, high quality tools should last longer that you do (especially hand tools.) Used tools can be just as good as new ones also.
Harbor Freight is good for consumables (sandpaper, tape, etc.) or one time use tools, but aside from that, I wouldn't shop there. Obviously you don't need to go out and drop 20k on a full Snap-on setup, but you should expect to spend some money. I've got a 155 piece mechanics tool set from Sears that has been supplemented as needed.
I got a nice set of 6 point Craftsman wrenches for xmas, I picked up the JIS screwdrivers from McMaster-Carr (makes all the difference in the world), feeler gauges, nice multimeter, Craftsman strobe timing light (found in a Goodwill for 5 bucks, works great), sync gauges, impact driver, torque wrench, etc.
Also, think about how often you see yourself using the tools before you splurge and buy nice ones. And if you are only going to use them once, see if there is someone who will let you borrow it for a case of beer.