@Will Parker I read his book (Never Split the Difference) a few months ago, and it was a real game changer.
TL;DR: I used the 65%/85%/95%/100% increasing offer tactic, huge amounts of tactical empathy and I refused to speak first whenever possible (yes, I had to embrace the power of the awkward silence)
For this deal, I made it a point not to speak first. However, the seller made it clear that I would need to throw out the first offer, and I went crazy low (started with a range around 65% of my target purchase price). I just knew she was going to hang up on me, but she didn't!
She said it was way too low, but agreed to show me the property after I explained that this was my "sight unseen" price without knowing anything about the condition or layout of the property. That got me in the door - literally.
Once I toured the place, I bought the seller coffee at a place around the corner with the goal of determining her motivations (while I acknowledged that my first offer was insanely low, I did not push for resolution of price in this meeting - we scheduled a follow up meeting several days later to hammer that out). I discovered that she was mostly retired and had been buying condos at the beach as her retirement plan. Also, she was a reader of the 7 Habits, too, and adamantly agreed that we needed to find a win-win.
She had owned this house since the mid-1990s and had lived in it for awhile initially. I told her that I may one day re-convert the house to serve as my primary residence, maintaining three income producing apartments (a later in life house hack if you will).
She acknowledged that the place was maintenance intensive at times but was very profitable. I said that, while beach condos may not bring in big time returns, they require almost no effort on the owner's part. I told her that as you get older, your time becomes exponentially more valuable, which is why less work for lower returns would be ideal for her situation. At the same time, at 28, I have time to throw into a project like this, but I need cashflow to get going with my REI "career." Again, win-win.
Long story short, she rolled the proceeds from this sale into a new condo this week using a 1031 exchange and has much more free time to spend with grand kids, while I have a potentially very profitable property that I could potentially live in one day.