It is only wind and hail coverage for the whole building - mostly roofs affected.

It's the easiest way to get taken for a ride by a contractor.

I've heard of agents riding around town just opening doors and hoping the buyer will pick something.

She has extra people living there, they are getting a free ride, they can pay for their own place to stay. 

Bigger concern is making sure you have enough buffer that its not going to be an issue riding the volatility out until the rents go up enough you don't care .

Most of Alberta now has a minimum $5k deductible for hail... and hail is roughly an annual occurrence for most everything near Calgary (especially Airdrie).

We let it ride & then found it was her brother going through a tough separation so occasionally he needed to get away. 

regarding roofs  pray for hail storms and then replace .. in those type assets that are really priced for cash flow.. values will rise only when rents rise.. as non of them will ever go owner occ.. at least that is generally what happens with this type of housing.. the value play is the tenant pays off your home and your home generates enough cash flow to break even at best and feed it a little bit over time.. then at the end of your mortgage term 30 years you now have say 2 mil of paid for assets the real money is made on these assets cash flow wise ONLY if you pay cash IMHO

My question is, would you just let this ride or does it make more sense to attempt to catch them while they're working and ask them to stop?

It's a ride that I don't care to go on, but hey, I'm probably a bit more conservative than most.