I have family in the Boston area and they vacation near Dover, a beautiful city. 

It is very easy to save money working in public accounting.I forgot what my dinner allowance was working at the big four 5 years ago in a major city(I think it was like $20?)

You can't genuinely expect other cities to not try to create the infrastructure, job desirability, living conditions to impede such progress.

Typically, most cities allow for 30 day minimum rentals.

In a dense area, such as in-town (city, dense suburb, etc) you should be able to find sales within a half mile. 

Depending on the price point, they may already be running targeted ads in cities/metros for buyers that may be looking for a second home/vacation home.

Overwhelmingly though, the weather and weather related things were enough to offset the negatives.So, I figure a much more interesting question would be Why do people live in New York City?

I'm a digital nomad who purchased a 4plex in Carson City, NV a couple of years ago as a buy & hold.

Good question - when Bigger Pockets leads reach out to us via out of state, we first define your specific goal with the BRRRR and talk through specific cities/areas that could lend itself to accomplishing that goal.

Post pandemic, the secret is out and investors can no longer 'simply' operate a nightly vacation rental in most cities and regions.