When I grew up and my toolbox was about as big as a lunchbox I rarely had that problem.
After I retired about 12 years ago I made it a habit to buy what I considered "good" handtools I might use whenever I found them on sale.
With 3 sons and daughter that could put in a patio door I always found someplace to "donate" within the family.
But lately I've ran across the same problem.
"Getting the right one" vs one that will do depends on what I figure is the "right one" out of my collection.
My worst conundrum is cutting metal roofing panels for various projects.
I've aviation shears, 40yr old tin snips, electric metal shears, jig saws, band saws, angle grinders with thin blades, circular saws with metal cutting blades, circular saws with regular blades reversed, "nibblers", chisels, reciprocal saws. Or last resort, chain saw
. I don't have a plasma cutter yet.
And many of them are stored in different places.
At what point do we stop buying new tools?