How would you handle

Tough one. It seems you feel slightly indebted for the help he gave you. That is a respectable aspect of yours. It seems you are respectful to him by taking the time to drop what you are doing to have a visit. Again, good on you. But he is not respecting you. In fact I would call it close to intrusive and invading. The fact that he thinks “we” can make a ton of money tells me he is playing the older and wiser card on a nice young lady. Personally, that would have been cleared up the first time it was mentioned to me. I also don’t like the fact that some guy is continually coming over “to visit”, let alone the later and later part. Him bringing a stranger shows even more disrespect. People always ask me if they can bring someone by before they do. I hate being suspicious of people, but in today’s world we have no choice. He very well could be popping by later to see when opportunity opens up for midnight auto. I could be a mile off on that as well.........but these things you don’t learn until it’s too late.

I do believe in honesty and whether it works out that you remain friends or part ways, he needs to know how you feel. The result will tell you the answers to any suspicions you may have. A friend will be fine with your feelings. A con will have a problem. Then you will have to get a dog.
Good luck Rani