I think quite the opposite... I always think, What an awesome deal this tool was, I'm so glad I have this tool vs having paid more for it...or.... this POS tool is crap, (or this tool broke) time to buy the good one after all...
95% of the time, the cheap tool does the job with 99% capability at 10% of the price. Think breaker bar, large sockets, long extensions, beefy ratchets, multimeter, etc. The only tool I purchased better the second time around was my wireless drill and impact driver (and it's a POS but Lithium, so it's held up great) I have busted some adapters doing suspension work, so I got a set of cheap 1/2 sockets for $20. Can do all suspension work no problem with my breaker bar.
A lot of the price of the high end tool is on endurance. How many times will you use that tool? If you make a living, or you use it heavily, yes it's worth it. For a tool I use twice a year...It's hard to justify nicer. $12 for single nice socket, $20 for 10 for cheap 6 sided impacts at HF... Satisfied so far..
When in doubt, I buy it cheap first, and if/when it breaks, or otherwise proves to be a crappy call, only then I buy better. There is some waste to my method, but I think I'm ahead of the alternative.