Buyer's always want to know how low can they offer? My response is let me pull the comps and check out sales and listing history. I try to pin a number that an appraiser will use. In running a CMA it is so important to note that unique properties are a challenge, to compare apples to apples. Horse ranches, citrus, groves, vineyards with land wells and septics, will rarely comply to square foot analysis, like it does for housing tracts.
Listing history and past sales tell me alot about the seller. If Mr. Seller bought at the height of the RE Bubble and has hung on for the last 9 years praying for a market/price rebound, Mr. Seller is Bullish, and probably won't budge.
Banks and Flippers are in it for profit, they might give a little discount, in initial offer but only if it has been more than 30 days on market, but don't expect repairs pretty much "as is".
Cash discounts? What can you expect if you are paying "All Cash"? Answer 10 day close and no appraisal contingencies. Banks don't care about your Cash, because in 30 days its all cash to them. The usual time to get a cash discount is if the property either cant qualify for financing, because of condition, age, unpermitted buildings, etc. if seller has disclosed all faults before buyer writes an offer, price reflects faults and buyer acknowledges this when making an offer. If seller does not disclose and buyer finds other issues affecting title, value or use. Renegotiation, cancel contract and or a price reduction is an option.
How much do you ask for? Pie in the sky number doesn't work well. How much does the fault devalue the property, will there be back fees to pay to bring the property to code?
Best way to haggle? Always split the difference and meet in the middle.