When boomers bought all of these second/vacation homes cheaply in the 80s it wasn't in places with huge demand from underhoused people.
These arguments need a little more consideration of facts rather than appeals to emotion.
https://www.coalitionforthehomeless.org/wp-content/uploads/2...
Nobody was buying second apartments in NYC in the 80s. Nobody was buying apartments period. I knew people with brownstones for sale in spanish harlem that they couldn't get $10k for in the late 80s. 80% of _storefront_ space in midtown was vacant.
People buying vacation homes in Florida or Vermont aren't responsible for homelessness in major cities.