Do NOT contact him about the payment. That would fall into you have become his "mommy" category. That turns men off.
Yes for his sister getting your help. IF.. and I do mean IF... IF you can help her without it being secretly about him. I have seen it over and over in these situations where the BS uses the family of the WS to gather intel or to keep the channel open... Do NOT talk to her about him. If you are just trying to be coy by helping her so that you can find out more about him, then you are only hurting your own chances. Do not LIE TO YOURSELF ABOUT YOUR REASONS EITHER..
Both of these questions you ask sound suspiously like you are seeking an excuse to contact him or find out what he is up to.
