You can sync any credit cards or bank accounts and it will automatically categorize reoccurring transitions (like mortgage payments or utilities).

If you are not there to monitor and work with them, you cannot know for sure whether they worked.Once you are skilled enough with home repairs, you can lead the projects yourself and hire help for a lower rate if help is desired.You will probably save tens of thousands of dollars over haggling with contractors over large jobs and make some good contacts along the way who you may trust in the future to work independently.

Also if landlord pays utilities that is something to monitor. 

Of course it’s a highly undesirable situation but I was left to make a choice out of a bad scenario.I have been project managing everyday remotely, buying all the materials and having them delivered and trying to monitor the work as closely as possible.

Monitor your account online..

On top of this, my tenants are making a mess almost every week and the city is sending notices to clean up the place or pay a fine for them to do it.I have a property manager and we have started to discuss cameras, so we can narrow down who is causing the problem.Does anybody have any recommendations for camera companies that are reasonable and would be easy for my manager to monitor?  

If I could pick the home up as-is and just monitor the situation while continuing to have it as a rental, would that be an option?

Give them a small job and observe/monitor to see what they say and how they perform.

See if you think, when using your criteria and common sense, if she can come up with her half of the rent every month after all her loans and other reoccurring expenses are paid....Just stick with your criteria and drill down on the debt terms more for the outgoing monthly to be sure it meets your standards..

@Alex Deacon how many months of observation did it take and what factors do you monitor to understand your market that well?