(oddly though they hadn't been monitoring value over the past 3 years and recommending raising rent gradually until I brought it up)  Anyway, they confronted the tenant when they paid their rent and told them that rent was being increased by $150 and if they didn't want to pay the new amount, they could vacate by the end of the month. 

Most often, you will overpay, confront significant logistical (and sometimes moral) issues and in the final analysis surrender all of your cash flow to big repairs or depreciation recapture when you sell. 

When my friend called Remax and confronted them they closed that office down completely.

If it’s just the constant barrage of endless texts, just block his phone number.If it’s the texts + you’re worried that he might actually carry through with his threats or start showing up to places you’re at and force a physical confrontation, seek a civil restraining order/order of protection (or whatever they call the equivalent in Canada).

I would also be prepared that when he tries to come back there will most likely be a confrontation, make sure to video it as he will most likely threaten you again. 

I did my best to help counsel him through his thoughts of depression and help him develop positive coping strategies to confront his negative thoughts.

Stopped the issue in its tracks without too much confrontation (so far...). 

Do I confront her sooner to let her know that I'm aware that her boyfriend has been staying there and that she's in violation? 

But perhaps use less confrontation verbiage than I've exampled

That violates Fair Housing laws.It also comes across as unprofessional and kind of confrontational.