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Totally Confused!

Dear Steve and Shirley, 

I am a middle aged single female who has been dating a man about five years my junior. He's a great guy has great values is a family man. But here's the problem. He can't afford to buy a ring. I'm not materialistic at all. However I am wondering if his inability to purchase a ring is a sign that maybe there will be other financial issues down the line since we met he has lost two jobs his car and his house all because he is pursuing an entrepreneurship which is currently not thriving. I have a Ph.D. a great job a home and I'm doing pretty well for myself. About three years ago I received a huge bonus check and at that time he stated whatever comes to either of us either one of us would be both of ours and he proceeded to ask me if he could use some of the money to buy me a ring. I thought that was crazy. I know that he's trying to get on his feet but it is draining to have to deal with this for so long. So here we are three years later and he's still working towards purchasing the ring. I've been patient with him paid his bills allowed him to use my car giving him gas money but I'm getting tired of extending my resources. Here's my question am I settling for someone who may just be a taker or is it possible that he's just having a bad six year break. 

Totally confused.