Hey there SG--- How well does your friend know this man? I would be very wary of renting a room in my home to a stranger who says he is or maybe even worse who actually is going through a divorce. But umm you actually said after/during a separation. Not good either. And especially one who offers work in kind right up front rather than planning to pay the rent. Once he is in you can't force him to do anything really. And personally I would rather have rent money to then pay professionals for work than count on someone with unknown handyman skills. What exactly does "handyman type" mean? Where is the evidence that he could do anything? What is his job at the moment? Hard times is the wrong answer. Do you want to risk the potential of having someone in bad economic circumstances that you do not know sharing your home? Could there be a nasty custody battle that might happen and you would be caught in the middle? All kinds of questions are circling around right now for me on this deal. It's moving much too quickly for my comfort.
Before you sign any kind of agreement you should become familiar with the laws in your area about renting and how difficult it would be to get him out of there if it something wasn't right.
I would suggest if you want a roommate to search for the right one. This may be exactly what you want, but you should at a minimum do a background check on him. I mean it sounds like you have close quarters there, just be careful. I don't mean to sound negative about what you are hopeful about but aren't you more than just a little nervous? What does your gut really say? You should have references and check them, know his employment situation, a lot of stuff before closing this deal. Please go slowly. You know where I am coming from on this so I had to say something. No one should get the benefit of the doubt when it comes to our safety and our money and our privacy and our sharing what we have worked to hard to create and preserve. And if he pressures you in any, and I mean any, way drop it, it's hot. Cheers, Wonder