Our relationship with money is often irrational.  It takes a lot of work to “think rationally” about money and untie the emotions that get into the way.  Studies have shown that for most people the pain of monetary loss is twice as great as the pleasure of monetary gain - so people irrationally turn down investment with less than a 2:1 chance of success, even at “even money”.  However, for a minority (small) of people, that equation is reversed.  These are the gambler chasing any high risk venture even with low success probabilities. 

one of the toughest money relationships I've had to deal with was in the last two years as I transitioned from direct real estate ownership to reinvesting sales proceeds into REITs. Unlike direct property investment, or even syndications, REITs as stocks actively traded are "marked to market" continuously. As a result I found it very hard not to want to "take profits" whenever a REIT I invested in rose 20 -25% in price. No such temptation exists in direct property investment, as the "fear" of price dropping just isn't usually there.

Btw, I would argue that utilizing your maintenance/repair reserves is indicative of SUCCESS, not failure.  All properties suffer deferred maintenance, needed repairs, capitalized items replacement, etc.  The fact that you prepared for those expenses rather than just hoped to have the cash available, or worse be forced to pay 18% on credit cards, is the genesis of SUCCESS, not failure.