One could ask 'Is it smarter to buy a fancy $500 tent that I can sleep in for free for months and months' - The answer would be 'Yes, that is a lot smarter right now, while portland laws have been temporarily waived so as to reward those who loiter, panhandle and camp on the city's dime'

One could ask 'Is this guy homeless because he made a lot of poor financial choices, like buying a $500 tent, when he only had money to buy an $80 tent?' - The answer would be 'No, the $500 tent was a good investment- it will last 10 years if taken care of.  It was the $200 shoes, the $130 pants, the $70 shirts, the $50 beer tabs, the $800 tattoos, the $140/mo phone bill, the $500 PS4 and the $220 vape that really let to his homelessness."