I month of vacancy and you're in the red for the year. 1 or 2 things go wrong (HVAC, roof leak, who knows) and you could be in a world of hurt.Breaking even in the duplex might just work as a house hack.  

The house has a termite issue and needs a new roof so we're expecting that it needs to be gutted to check for any rotting wood.

YES-they can set you up with auto-email, but at the end of the day, they are never going to be as motivated as you and submitting offers is not going to happen EXACTLY when you want it to.Since getting my license, my investing success has been through the roof.  

In addition, lots of drywall, flooring, kitchens & baths to do, likely new roof, repair wood rott, brick pointing, windows/doors.  

The other way is to piece out everything that would be considered capex; furnace, AC, flooring, carpet, windows, roof, parking lot...  

A great quick turn depending on foundation, roof, HVAC and electrical/plumbing.

Windows, doors, roof maintenace (minor), potential need for HVAC in 5 or so years.

Then what if the roof leaks?

We replaced all the windows on each house and with this last one, we replaced the roof and all flooring as well as a few other things to bring it up to a nicer standard.

I have used him on 2 other properties and his estimates have been fairly good so far.The electrical and plumbing that we can see is updated and the roof is only a 2 years old.