STARS: How to Help Someone in Need

I am currently in the process of helping someone get back on their feet. I won't mention their name. I offered, along with my uncle and now they are willing and so are we. 

I want to ensure they are headed for gainful employment: current job, new job, temporary unemployment or permanent disability. I want to see an end goal and effort. 

I also want them to give me an update of where they are trying to live and a summary of where they checked. Hotels and friend's houses go only so far. 

I am willing to give them money for odds and ends but I don't want them to take advantage. Effort must be demonstrated before me first and then I have an amount (like a stipend) I will help them will. I have discussed this with my uncle. 

I am confident this is the moment of truth. This person will find their footing or they will be disillusioned and not ask for my assistance again. Either way, I will have did my part.