You can prevent this by requiring them to add you as "additional interest" on their policy.

Additionally, I'm hearing at meetups that this could extend to multi-fam under 4 units as well, although I haven't been able to confirm.I work exclusively with smaller investors in the multi family space and would be happy to chat more about it.

Very interested in the Cleveland/Ohio market in addition to a few other cross-border cities closer to Toronto. 

Your best bet is to ask for referrals from professionals in the space: realtors, other investors, this forum, FB groups, etc.

Here's the deal: You don't need to withdraw and return the current security deposit just to collect the additional $100.

Given that you're not married, that adds some additional complexity.  

million in addition to their investors (who expect a reasonable rate of return) by keeping the rental rates at a fraction of the market rate?

A PM offers so many additional services in addition to things you cannot do yourself - like simply having a 3rd party between you and the tenant.

I would have contacted the locksmith tech to get additional details before assuming it was tenant damage.

I do have additional coverage for the sewer since I knew it may have issues before I bought the property.