Seller Financing?- Random Conversation?

[Victor G.]

So I am an aspiring real estate investor, but to get my feet in the game I've been looking to House Hack my first home. Well last night at I was talking to a guy at my job who has been wanting to retire basically and he was telling me a story about how he's not sure when he will because of issues he has with his properties and how he has pulled money out of his retirement fund to buy properties, in which he has a total of 10.  The situation he is in is a mess where he does not want to sell because he keep getting low ball offers and he'll lose money selling with an investor he told me. He was advising me that being a landlord was the worst mistake ever, "Their Problem is your problem" and every one is against you including the courts, cops, and etc.. However in the back of my head since I've been studying thanks to BP, I was thinking wow this could be a good time to implement seller financing. 

The issue he has mentioned with his properties is vacancy including one that has been vacant for 2 years because he was doing the rehab himself and him having poor tenants. The properties are in Upstate New York about hour away from any metropolitan city. He has mentioned he is unsure what he wants to do because if he sells he would lose money and have to pay taxes, however when he retires he doesn't want to deal with the headaches of being a landlord. Even though I shouldn't give advice I told him about the 1031 Exchange and how he can avoid Capital gains when he sells the properties, which excited him because he wants to get a nicer home with land so he can do farming once he's done with work. 

Basically what would be some good ways for me to approach him about selling me his properties through seller financing without offending him (LOL) ? Would this be a bad idea even with the vacancies issues. 

[Jason Dillard]

@Victor G. Ask him how much he gets per month after all expenses. The next question is: If you could make that much or close to it without any work or worries, is there any reason you wouldn't do that? Then listen. Then ask another question. Then listen. Ask. Listen. ...for about an hour. Then present an idea. He finances to you. He partners. He trades. Something that will move him to a better position and move you to a better position too. BTW, if he disposes of property for a less than his basis, he won't pay tax.