I have plenty of tools I have purchased and perhaps not used as much as I should. However remorse would be pushing it and I love my tools, not to mention with the exception of my circular saw (which I got for peanuts only a couple of months ago) they have all proven their worth several times over. I try not to have any exotic stock for the bread and butter side of my business, I might have overbought on the small network switches but if that saves me having to punch some belkin dross that someone got in the real world into working order it will have been capital well sunk.
The worst I have is junk I have fixed up just because I was bored that afternoon or junk I was given so the other person does not have to look at it.
That said, despite splashing out on an "action camera" (got one of those SJ4000 want to be gopro things, lovely little thing it is) the other day my pool of fun stuff money is getting to be reasonably sized so I might be able to add some cheap Chinese tat like a cheap Chinese CNC, variable frequency drive or autotransformer despite not really having the most use for any of them right now.