The current owner is a family friend that’s been in the business for 30+ years but is very old school and still runs the business off a system he coded in DOS back in the 90’s.

I'd first start by reading 3 books....the Millionaire Real Estate Investor, HOLD, and FLIP....all within the Keller Williams systems. 

I haven't evicted one of my tenants through the court system since 2014.

However, if the property has a newer roof, newer windows, updated plumbing and/or electrical, updated heating system etc., it is possible that this number could be adjusted downward. 

This should be able to be completed without disturbing the upstairs flooring system too much.

What are the equivalents to “www.cozy.com” or www.rent prep.com” etc, what systems can be used in Canada to set up rent collection, security deposit and other payments?

“Right now, during the emergency, we have an eviction system which is slow but at least it works.

A facetime video will not tell you if it needs a new septic system or HVAC, or if there is a snake den on property that needs dealing with.  

Eventually a person working for the state was able to send in a correction form to the IRS to fix that problem...but it took a lot of effort on my part to work through the system to see who and how the monthly board payments could be changed from salary which is taxable to board which is not.The other time some folks that I never met, have no idea who they are, or anything about them, used my SSN as theirs for work they did at several chicken processing plants. 

We have discovered some of the downsides to septic (having to replace a full system now!)