The work is taking a long time because he is trying to milk it until his kids go back to school.

Now he has another child and it's needs to deal with on top of this, diapers, milk, baby items galore.A contract comes through, he starts getting the debts paid and off his back, but he had to take a job at half his previous pay, and he can't make enough to cover the bills.

Money Mustache's voice derisively going, "Wah!!!

And I'm sure this guy would milk you for it!

I wouldn't just give out money unless my lease states I would refund the current months' rent--- you don't want to give out money and tenant think they can milk you for more money or try to use you giving them money as you admitting liability to get more money out of you/insurance.As for what to do, sorry I can't be of much use there.

I'd like to milk as many free lunches out of this as I possibly can (lesson I learned at UC)...:-) 

@Eric FitzgeraldIf you haven’t already, read up on mr money mustache.

You can drive your Hummer across town for a quart of milk and fly your private jet from SFO to JFK just to catch a Broadway show, but plant a few trees in Brazil and you're OK.

A bit of diversity should be required, but if you are knowledgeable and successful in one RE niche (or any market or niche for that matter) I say stay there and milk it for all its worth.

If you haven't already, I would check out Scott Trench's book Set For Life and mrmoneymustache.comAlso, although not directly relevant to your situation, here is a specific article from Mr Money Mustache that has a lot of really good points.