The basic ethos behind both articles is fine. It's rather like the podcast where Steve talks about carrying more money on his person to be more in line with the mindset of wealthier people who carry more money. The $10K hotel room isn't a great example as it strays into the perception of value rather than measurable value. I wouldn't stay in a $100 hotel room either - I have my own idea about hotel price/quality balance. Same with $30 shoes. I'm sure others do too.
The problem with communicating the ideas in the articles, is that readers will get bogged down with value, perceived value and waste. They'll ask if it's worth spending 10 times as much just to get something 10% better. Also it encourages the concepts of 'good' spending (e.g. having a $100 hotel room and giving the $9900 to restore sight in 3rd world countries). And 'bad' spending - spending $10k on a hotel room where the staff are better dressed. There really do exist things that are a waste of money.
I think the ethos of the articles is fine but the analogies make it difficult for people to get past accepting the basic message and the law of diminishing return.