Living with (a friend's) regret

[Nick Bruckner]

I recently visited my best friend from high school in Chicago. I moved to Alaska fifteen years ago and we haven't talked a lot over the years, but it was just like old times. He has a master's degree from the University of Chicago, and has always been employed but has been renting his entire adult life. He shared he's wanted to buy for years, but has always been intimidated by high prices and high interest rates. I am an investment oriented real estate licensee in Alaska and I talked to him about FHA loans and the possibility buying a 'two flat' (Chicago area duplex) to offset his monthly mortgage payment. It's maddening that he could've built so much equity in the past 15 years but he's been on the wrong end of the equation due to that anxiety about making the plunge. Sometimes its hardest to rationally present helpful information to those who you care about most deeply. Have you ever had a similar experience? Any tips?