How do you break the ice when talking with someone whose house you're wanting to buy? How direct are you? Do you start by talking about unrelated things and then slip it into the conversation? How do you obtain results without wasting time? I'd like to hear success stories and lessons learned. 

I'm not super experienced in this, so take my advice with a grain of salt.

I've made a few purchases like this. One was a hoarder house and the sellers were too embarrassed to let anyone see how they were living. Another was a woman that wanted to sell discreetly because she used to work for a REALTOR and didn't want that REALTOR to know she was selling the home without using her former employer. Two other large properties were owned by older people that wanted to slow down but they were worried about paying the taxes.

In all of these situations, I started by being honest. For example, I told every single one of them what their property would be worth on the open market before I ever expressed interest in them myself. Then I told them what I was willing to pay for them. Then I provided them the various options available (Subject To, Owner Financing, Lease Option, MLS, traditional sale on MLS, etc.)

I honestly think they chose to go with me because I was honest about my intentions, I gave them a lot of options, and I kept their needs front and center. Every single one of them sold to me at 20 - 60% below market and a couple of them chose seller financing to avoid the taxes.

Instead of trying to convince them to sell to you, listen to their needs and find a way to help them.

@Devin Bost

Start by talking about the house, then their situation, market values, come to a conclusion on price, ask to buy the house. Of course, I’m more straight forward than most people.

If it's an off market listing always find a way to compliment the property. If it is in disrepair say it has "potential". Give them a free cma or report on what the property is worth. Always leave them with something valuable even if they don't want to sell.

By "what the property is worth," are we talking about the After Repair Value (ARV)? If I give them that figure, then I'll need to utilize the estimated repair costs to justify buying at a significant discount (60-70% of the ARV or less), which would also lead to me needing to give them my margin. Am I following correctly? I would think that could backfire.