Interest rates going up is impacting the ability of renters to migrate into buying houses.The 'increasing tenure' bullet point will undoubtedly impact future sales and refinances. 7-10+ years down the road people who bought a house within the last 2 years at all time low rates will not be inclined to either sell or refi unless they have to.

My inclination is that I need to let her know now before this goes to court because she could get an eviction on her record and that seems unfair, especially if she is financially able to cover the rent.

So many of them are, in fact, too busy to work with buyers, and/or have no inclination to do so. 

If you haven't spoken to RTB already, I'd suggest you phone them and see what they say about the situation.If the tenants threaten to move out I would be inclined to let them go - the rental market is tight right now and, based on their lack of awareness about household issues, they may very well cost you more money down the road from some other issue.

Going forward, the goal would be to raise the rent once a year consistently on Jan 1 of every year based on market rents.She is a really great tenant, so I am inclined (as others on this thread have pointed out) to put a premium on her and try to keep her in the condo.

If the roof is close to 15 years old (or older), then I'd certainly be more inclined to tell you to consider paying for it yourself, as the roof has really reached the end of it's useful life in most cases (especially in heavy wind/hail prone states). 

I would be inclined to have you save a little more and wait for a property in one of the top tier communities.

I'm inclined to work with them, and make it clear that next months rent is again due on the 1st.  

I am also inclined to wait a little bit for things to cool before buying another STR, if I'm buying at market value.

My inclination is to avoid like the plague but I also don't want to window shop a great opportunity!