I wouldn’t go near the “proof of deals” question. It’s a little insulting. You can get that info as you discuss his “best deals”.
First question I would ask is… How did you get started? And I mean everything, what he did before real estate and how he broke out.
What did you learn from your first deal?
How did you get your first deal?
What mistakes did you make?
What’s your best advice for me?
How did you build a relationship with your bank?
Do you have any before and after pictures of your properties. (this question alone can be priceless) The guy who gave me my start specialized in taking single family homes that were in commercial areas and turning them into office buildings. The pictures were an eye opener for me. He used to convert them by using brick or Dry-vit on the exterior and the transformation was unbelievable.
What would you do different if you were starting over?
Will you look at some deals I bring to you for your opinion?
Do this only after you know you can trust him.
What was the single best project you ever did and why?
How would you start if you were me?
Finally, If he’s the real deal tell him how much you appreciate his time. And here’s the most important part… DO NOT WASTE HIS TIME.
These guy’s get lots of people who ask lots of questions and do absolutely NOTHING with the advice they’re given. Your mentor will drop you like a bad habit if he thinks your wasting his time. Listen to him (again if he’s the real thing) and follow through on his advice. As he see’s you doing so he will become more excited about helping you. You would be amazed at the number of dopes that get an opportunity like your’s and do nothing with it. Keep him updated but don’t be a pain in the ass. There’s nothing worse than offering to help someone and finding out you just adopted an idiot who can’t figure out how to get comps on properties.
Good luck, make the most of it!
One other thing… Excellent idea placing the ad, really shows your not fooling around and my guess is it impressed your future mentor!