We have held a rental property for over 25 years. Since we refinanced it, we have been making a cash loss after paying mortgage and taxes. If We were to gift this rental property to our son this year can he sell it ne...

If you buy, occupy, and are PCS moved 6 months later, that is beyond your control, and nobody really checks that.  

Especially, that there is always losses for the first year of owning a property - it starts cash flowing much later.

I simply paid it out full 3-6 months later. 

Did they need more of a wake-up call that sooner or later they would have to leave?

I'm confident I can refinance that property 6 months later at an ARV of $425,000. 

Asbestos was later discovered and now rehab will be much more.  

Initially our landlord (or representative from the real estate organization our building is owned by) was responsive and told us that she would send out a maintenance repair which didn't arrive until I followed up with her a little less than a week later about an update.

Initially our landlord (or representative from the real estate organization our building is owned by) was responsive and told us that she would send out a maintenance repair which didn't arrive until I followed up with her a little less than a week later about an update.

So I have a two-flat that I'm house-hacking and I'm replacing the floor in my unit to be able to rent out later.