I've seen too many demo crews cut into or otherwise damage the structure, like cutting trusses, etc....I would just have the chimney crew do everything... 

I’m curious if truss delivery is still taking a long time.I imagine the recent storms have set you back on your timeline, and wish you clear skies going forward.  

I'm using my phone and text to speech.

And I am for freedom of the speech to the point that I will defend the rights of others to use ad hominess to attack me.

That's why we have Freedom of Speech, versus tyranny where people get their heads cut off if they speak unpopular things.

The time for me to go to Lowe’s or Home Depot to get truss hangers and nails because the investor only got wall studs and roof truss is still a costly mistake when you look at drive time.

@Hieu Bui Your numbers are a bit off... roof itself will be close to $10k.. you have soffit rot and that might be rotted inside into the trusses... yikes..I saw ceilings that were leaking as well...Personally, I’d get a waste contractor bin.. remove all the crap, take a log screwdriver and then start poking around... you can see what’s not visible...Once complete, do a materials cost list.

There is roof damage, probable damage to the trusses, and the water line busted.

Thermal scan is the way to find exactly where the leak starts and then open up to see what's inside, A/C condensate line, plumbing drain, water supply...gutter overflow or even a roof leak running a rafter/truss...it could be any of those. 

When his lease is due to expire give him enough legal notice and kick his monkey a** out of the unit (don't actually kick him it's a figure of speech lol)  That's a bad tenant you may have been able to screen and weed out with an experienced PM.