Off the top of my head, if I'd bought an i3 instead of an i5 back in 2013, and replaced it with a brand new i3 two years later, I'd still have a slower system than what I have now, and I'd have spent more money. (2x ~$130 CPUs instead of a single $200 CPU, two motherboards instead of one, etc.) Heck, for the 2x i3 rigs cost, I could have bought an i7 and been REALLY happy.
So there's definitely some circumstances where "go big or go home" is fiscally responsible.
Or maybe the question is whether to get a new low end system every 3-4 years vs. a high end one every 7-8 years?
Would a Duron in 2002 -> E6300 in 2006 -> i3-540 in 2010 -> i3-4330 in 2014 be better than a OC'd Athlon Barton in 2002 -> Q6600 in 2008 -> i5-4670k in 2014? That many platform and RAM upgrades would mostly make up for savings on CPUs, I think.
Thing is, the high end consumer CPUs (consumer i7s) are about 4x as powerful as the lowest-end Pentium/Celeron desktop chips, and IIRC that's been a pretty consistent spread for a while. (At least as long as there's been consumer quads.) And we've been seeing relatively minor bumps in speed every generation for a while now. So you have to go quite a few generations back to find a high end CPU that the current low end can really embarrass.