@Philip Bashaw Hey Philip,
I wouldn't even talk extensively about real estate or future plans right off the bat. Take him out to lunch, see what kind of guy he is. Someone mentioned above About due diligence, A lot of information can be gathered from diving right into who it is your siting across the table from, everyone has a story, learn his story. I believe you said it above, Listen intensively what he is saying to you, most likely he will tell you what his plans and goals through natural conversation . Don't feel the need to try to take control of the meeting and try to impresss him, he has $25M that is an impressive accomplishment in itself. Remember he has $25M, that doesn't just fall in your lap(unless it's a trust fund or in heritence) Just from getting to know him in the initial meeting just asking simple questions. I wouldn't jump the gun and get heavy into numbers and projects, and try to impress him. Your goal should be to try to impress him with who Philipis asaperson, real estate is a long term relationship business. Do show him the kind of person you are, so he can begin to become comfortable with you. It comes across too desperate off the bat trying to convince someone right away why they should invest with you. Your a smart guy who has dealt with all different kinds of people, work on the relationship. The rest will come in the 2nd and 3 meeting. But the very first thing I would do is what @Karen Margrave suggested and make sure he is who he say he is and he is for real, last thing you want to do is waste your time. If he is for real, remember he is a person like all of us, I am multimillionaire, I have friends who have net worth that exceed $100M and by having a conversation with them you would not be able to tell because most of them are very humble down to earth people. Don't feel the need to pressure your self or try to impress, he will be most impressed with the kind of person you are. Philip you seem like a great guy, go into the meeting be yourself and get to know this person. It could be the beginning of a wonderful friendship and business relationship. Wish you the best of luck and keep us updated with how it goes.