Where to Draw the Line

[Megan Hirlehey]

Hello,

My best friend's mother is currently going through a divorce and trying to sell her house. She just dropped a potential buyer after over a month of going back and forth with low-ball offers, inspections, negotiations and nit-picking about the property (Her home inspection was sound, the house is just a little outdated cosmetically). Her life has been turned upside-down enough by the termination of a 20somthing-year relationship, and now she is trying to get what is left of it back on track without being ruined financially.

This got me thinking, where do you draw the line? Obviously, no real estate investor would ever make money if they paid full/asking price all the time for everything as there is no room to build value (although you can generate passive income from rent I suppose). But at what point does the investor step back and say "Ok, I'm crossing the line from 'Getting a good deal' to 'Screwing someone literally our of house and home' "? I assume it's a mostly personal decision, but I am curious about how seasoned investors deal with this aspect of the industry.