More than anything this is a psychological thing.

Sadly, my uncle had some psychological issues and at the time of his passing in October 2014, he had allowed the house to deteriorate to the point where it didn't even have working restrooms, the roof was missing in places, about 70 dead mice were found throughout the property dying after eating electrical parts from knob and tube wiring, the entire basement had over a foot of standing water and we found several nests of black widows. 

I also read an article about the psychology of pricing / buying.

I'm interested in the psychology of investors who think our interests are not aligned with theirs when it comes to turnover.  

Sometimes playing along with someone's psychological weakness (like that need for power) can be a strategic decision.

To me it seems like investor psychology...it will be much more likely to stick in the mind of a seller more than just a letter by itself...Would others care to share their experience if you've done this, and for those who haven't, what do you think about it? 

Is it worth it (psychologically and physically) to hang on to this loser property?

I don't know for some reason i find Gurus and mentors to be different to me psychologically.

,The question you ask is the source of much disagreement.Since you posted it under "Investor Psychology", I'll answer this way:The "consumer" mindset says, "be debt-free".

I realize that sometimes the psychological needs have got to trump economic rationality, but it seems to me that this shouldn't be the case when you're just building your portfolio.