It is not guaranteed money, the properties are often not in good condition, and CMHA is difficult to work with.

If you won’t hire a PM I’d send something like: You’ve been a great tenant but because of market conditions the rent will be increasing to $x at the end of your current lease.

He did all the rehab in the beginning when he bought the house, that's why its now in a stable cash flow condition. 

If the tree was a straight tall tree that did NOT overhang the property and it fell across the property line damaging your garage then that could be the neighbors liability if they knew or should have known it was in poor condition.

I think their general stance is going to be to go with whichever comparable property has the greatest degree of similarity in terms of (probably, in this order): location, age built, quality of construction/current condition, and square footage.

The rental yield is pretty low compared to its value, and selling now while it’s in great condition could help you avoid the stress of managing it or dealing with wear and tear.

Without comps and a credible assessment of the condition, it could be a grand slam or  possibly 80k over what you should pay.

Did a second walk through this weekend to make sure everything is still the same condition as the first walk through.

You will want to provide basic amenities like included washer/dryer since living conditions are already less than ideal with that many roommates so you don't want the added hassle of them needing to go downtown to a laundromat. 3.

Without tenants it's easier to show the property and the condition can look better than if tenants have their stuff everywhere.