Tell a seller everything thats wrong with their house or no?

[Ralph Stowe]

I went to a local gathering for a guru who is pretty successful and has developed a following.  His strategy when negotiating with a seller is to justify his low asking price by pointing out "The house needs this and the house needs that, and that could all add up so that's why I can't go much higher on my asking price..." 

Now I went to ANOTHER guru who is also successful and has a pretty big following in town, but HE says, "Don't tell a seller everything that's wrong with their house. It upsets them. You're insulting their most prized belonging. Let them give YOU a number first and work from that. If they absolutely won't give you a number, work it backwards from,  "Well I need to make __% on this, plus I have X costs involving ____, so by my calculations, I'm somewhere in the neighborhood of $____.  and don't deviate from that too much. If you go up $20k or more, the seller thinks, "This person just tried to rip me off for $20k or more!" and won't want to do business with you." 

In your experience, is it more successful to point out all the houses flaws to justify a lower offer, or simply sympathize with the sellers situation and leave the house flaws out of it?

[Corby Goade]

There is no right answer to this- as you've seen, you can be successful using a myriad of strategies. In my experience, the most important factor is building trust and rapport with whoever you are negotiating with. If you do that, you probably have some leeway to approach more difficult conversations, BUT if they don't like and trust you, they're going to be easily offended and pull back or back out altogether. 

My market is super competitive and, especially with wholesalers, if someone is talking to you- they've picked you for a reason, most likely you aren't insulting them or pressuring them. If they are in a pickle, chances are they've got a stack of postcards on their counter from wholesalers, if you don't build rapport, they'll call the next one on the stack.