I would make it unpleasant for someone that overstayed their welcome.I have been doing this for about 10 years and have never had any cause for concern about someone not leaving when they were supposed to.I have a fishing team staying at the house that are in a tournament.

The four richest men in in the state died poor because they could not stop themselves from buying more and more land to develop even while the boom was crashing around them.

@David Ward Focusing strictly on investment properties and putting down 20-25% like you mentioned Boston is an expensive market to begin with then you thrown in the low interest rates to keep the economy from crashing and you’re seeing prices 10-15% higher then last year alone, it’s a terrible time to be a buyer unless you come across the perfect deal but those deals probably won’t even hit the sites before they’re already sold I would suggest hitting Zillow and contacting the most popular realtor/brokerage in the area because that’s how you’ll find that perfect deal.

Is there a mass exodus from NYC yes I’m one of them bought a new construction 1.5 hours away are the prices reflecting the mass exodus sadly no or maybe not yet..I had a similar idea as your wife figured let me buy a condo in UWS use it for Airbnb and on days I work late have somewhere to crash near by but I’m just seeing modest discounts on prices in certain areas nothing to get excited about...

Crash or no crash, look at numbers!

Will a future housing market crash affect hard money lenders willing to finance projects or purchases? 

Whether the market crash or not, the fundamentals are important.

Market crashed a year later and we didn't "break even" until 13 years later.

Market crashed a year later and we didn't "break even" until 13 years later.

They are neoliberals--aka cronies of Big Business/oligarchs--using populism (in this case, liberalism) to crash the housing market so that small landlords are forced out of business and the biggest developers and speculators own it all.