Buying a House - Making a low-ball offer to a "DESPERATE" seller... Advice???

First set the price you are willing to pay in your own mind. Sounds like $250K. Offer what you believe will be his dead bottom. Might be $190K. He will(more likely than not)reject that offer, be insulted, call you names, etc. Do not be disturbed, this is normal. If he doesn't counteroffer, ask what he would be willing to accept because you aren't interested in paying much for his property. This will break the emotional barrier of real estate sales and purchase. He will begin to think in realistic terms. He took a risk and it didn't pan out, time to cut his losses. He will be ready to deal with you on a strictly business level now. Hold your number. Be ready to walk away. He will more than likely lower his current list price but not to where you are. Come up a little off of your initial offer, say $220K. This will cement in his mind that you are deal shopping. He will probably give you a final offer that is higher than your $250K. Tell him $250K is your final number and do not, under any cirstances, contact him again. I had a purchase that I walked away from and 6 months later they contatcted me and we made the deal for 10K less than my final offer.