Some dogs suffer from separation anxiety and do this. 

The issue is this negative initial cash flow increases the amount invested which will impact ROI forever.I do not do flips, but if I purchased this property I would be flipping it rather than suffering that level of monthly negative cash flow on that cheap a property.Regardless if you rent or sell, add a closet to each bedroom.  

Madison (senior living) and Nelson (student housing) have suffered from a combination of poor planning and poor execution, as our income from those investments has either stopped or diminished.

We both agreed.Tenant argument to me has always been, they are unable to pay rent due to PTSD suffered when they had several relatives die. 

We went way over our expected budget - by far our worse budget miss ever (remarkably we were only 0.5 week over our 2 month timeline).Using my rule, take the estimates and double them then add for lost occupancy and that is what I would be seeking or the owner have the work done using licensed contractors and do the work, take the risks, and suffer the vacancy costs.If you purchase having to do the work and your appraisal can handle it, the credit at closing is superior to price discount.  

I expanded fast and my reserves for sure suffered temporarily ( was taking some reserves for future downpayments) , but am aggressively building those back up, while growing my personal savings bucket, and do very strigegent tenant background checks and references.   

Afghanistan, Iraq, Libya, Lebanon, Iran, Ukraine, Vietnam, Korea, Venezuela, Cuba..... on and on the list goes who have suffered, seriously, via US interventionism. 

Landlord has to suffer the loss.

That's THEFT, and you should suffer your choices. 

It goes deeper than that.NYC Liberal policies, including strong tenant protections, increases the risk of failure so much that the risk far outweighs the rewards.Financial ruin is just around the corner for the small Mom and Pop Property Investor that it doesn't make sense for them.The Tenants will have free Attorneys that are bent on delaying eviction cases so long that it stretches into years while Mom and Pop suffer from lack of rental income and still have to pay all the bills and do the management.Additionally, the increase in homeless living rough in the streets due to Sanctuary laws causing a lack of shelter beds, then evicting shelter residents after 30 days creating more homelessness, policies that tie up the Police's ability to arrest perpetrators, etc. only causes Mom and Pop to sell out at large discounts to larger Landlords who are capable to use Economies of Scale to eek out a profit.These larger Landlords will eventually turn a much higher profit as the pendulum will eventually swing towards the middle when the NYC Voting population eventually realizes that it's not a conspiracy of the Rich that's causing the Wealth Gap to increase.It's the same liberal laws that encourage people to become lifelong tenants, small Entrepreneurs (including Property Owners and small Mom and Pop Businesses) to be destroyed, and Rents to rise astronomically as housing becomes scarer even when the population declines by as much as 7% in the last several years.