In my market there are 2 reasons that keeping is smart.  1) the historical long term appreciation is on going, going back to when records started tracking the appreciation 2) the property tax is near fixed cost.  

January is historically the lowest demand/income month so when a cancellation happens it hurts more.

There, now it will appraise as a FORMERLY illegal bathroom, current storage closet (appraisals are about the CURRENT property, not speculation about what the property might once have been historically). 

Quote from @Brandon Weis: We have historically had in our leases that renter's insurance is required, but we had been lax on enforcing it because owners didn't really care and not all tenants had it.

Portsmouth, known for its historic charm, offers higher prices but strong demand for both multifamily properties and short-term rentals, with premium rental rates for well-located properties.

My wife and I own a beautiful historic home in a small, charming town in Northern Virginia.

This has become challenging due to an increased interest in the historic district in Dubuque due to revitalization plans that include 18 million dollar investment into the historic downtown area. 

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, 1-3 years for positive cashflow, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, immediate cashflow and at the lower end of relative rent & value appreciation.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

This caused a historically unique opportunity for investors - they could buy Class A properties and immediately cashflow when renting them out.This couldn't last forever, and it didn't, as excited new investors drove up prices.