Why do folks spend more on electronics than on speakers?

It's not about money so much as getting quality speakers that benefit from the quality of the electronics. I think it is easier to get quality speakers that can reveal the quality of the electronics than vise-a-versa. Picking speakers gives you the capability of getting the sound you want - your choice of electronics seals the deal or, if poorly chosen, sinks the boat.)

I have spent vastly more on electronics than speakers. My DAC alone is about 10 times the value of my speakers.

Partly this is because I have a small room and listen in nearfield, and so I only need smaller speakers, which are inevitably less expensive.

But mostly because I have always found that the biggest improvements - as opposed to biggest "difference" - can mostly be made through electronics before speakers.

You can buy an extremely good pair of speakers well below $10k, and for bookshelf speakers well below $5k. But it doesn't matter how good your speakers are, if your sources and amplifiers are unsatisfying, then you will produce a mediocre sound, regardless of how good your speakers are. The better your speakers, the more likely you are to be unsatisfied with the results if the electronics are not up to the task.

I have owned a lot of speakers, and a lot of electronics over the last 30 years or so. I have always found that once I have a pair of speakers I like - and these have usually been not all that expensive - the biggest improvements have come from maximising the source - DAC, turntable, phono stage, - and then the amplifier. Throwing money at expensive speakers will usually produce a very different sound, but not necessarily a better one.

This was reinforced to me only recently. I was very happy with my relatively modest speakers, but felt that my electronics deserved "better". I bought some speakers literally double the price of my previous speakers, which had been very well reviewed, and which had impressed me in a store demonstration. After living with them for a while, I went back to my cheaper speakers, which were more musical, more engaging, and just as capable of getting the most out of my system, whose value is approaching six figures, of which only a small fraction comprises the speakers.

Right now, speaker capability is far far more than the amplifier capability, and that is the reason.

My guess is that for many rooms, having more expensive speakers (often correlated with bigger boxes and deeper bass extension) is not yielding the same increase in performance as an increase in the quality of the electronics. 

In Japan or Western Europe, people have smaller living spaces and it is very rare to have dedicated hifi rooms for people living in big cities. It must be the same in New York, SF or Seattle. It might make sense to have transparent, high achieving speakers like Spendors, ProAc and others at 6-8k and have excellent upstream components rather than the big Wilsons in the living room. And the missus probably wouldn't like to have big boxes in the middle of a 300 sqf living room ;-)