Needless to say, a lot of STR operators are in dire straits right now here in Florida.

I am a high school teacher and both children who were born in the United States have earned strait A's in spite of the challenges that extreme poverty and fear that their parents could be deported present.

The location is great, but the place is in dire need of some TLC.  

It will need septic, and furnace work as well as TSP scrubbing all the walls, paint, flooring, and the kitchen is in dire need of gutting and replacement, and the bathroom could use a gutting too.

But I would only touch them in a dire emergency situation. 

Its not quite that dire :-) Dividend income from the US entity will have a US withholding (5 or 15% depending if it is a child/subsidiary company or not) and this will be credited against the Canadian taxes on the dividend income.

There isn't a dire need to find an accountant local to you.

My first and only rental was built in 1969 and the chiminey is in dire need of "repointing", sealing, bricks replaced, etc.

Yes, it's really scary, because the outlook for those that get it is so dire. 

I've also heard having a list first is dire.