I'm so torn!!

Became a widow almost 6 years ago. Had a great marriage and always pictured myself with my late husband until we were really old. However, there was another plan and ever since I can't seem to make a final decision when it affects my personal life - it's like I lost all of my confidence in my judgment.
I have been seeing someone for 4 years and we have been on and off (due to me walking away). Long story short - I don't trust his personal judgment and credibility all the time - he says what I want to hear instead of the truth many times. However, he is very loving and we have very good chemistry and I do love him. But---he is in a difficult financial situation - unemployed but may get a job soon; but that job won't pay much....he has no savings or anything else and he is 65 and I'm 59 years old. I am a professional with a very good income and fairly sizable assets - however, I'll need those funds to support myself and help my 2 kids as well.
Every time I'm ready to break up for good - i stop short of that and the few times I did actually break it off, we ended up reconciling within a month or so. It's like my heart is saying one thing and my head another since I know he is a potential monetary liability for sure and I suppose i'm not convinced he wants me for what I have and not just who I am.
Now he wants to marry me as soon as he gets a job, including the one which which doesn't pay much and he keeps on saying how happy he is that his life is going so well. But I am so depressed!!!
I just want to be settled with a partner already move forward with the rest of my life, but I want to know that it is with the right partner and recognize no one is perfect, including me.
Help please.