Update: He moved around the corner from my apartment, so I took a chance and went and saw him again, this time for just therapeutic massage. It was OK but not great. He again seemed like a nice, sensible guy and expressed willingness to do escort services again if I ever wanted. A week later, he once again asked me for rent but was gracious enough when I said no.
Bottom line for me is he's conveniently located and has been fun both times I've been with him, so I can put up with his easily declined requests for rent money. The fact that he's tall, good looking and a hot top are major pluses, of course.