Is it the worst time to close on investment property ?

Investors can be their own worst enemy when they take hard line stances. 

Worst case, after about $8,000 of legal fees and surveyor expenses and 2 years of your life gone forever, IF you win, the judge will make him buy a small sliver of your land for a cheap price.

Worst I've seen is friend's dog chew trim.

Leaving your dog at home while you go on vacation is the worst, bring em! 

We can tell ourselves all sorts of stories about why things didn't get done as they should have but at the end of the day it's our property and our responsibility. 

My best advice for any future investments is to always plan for the worst.

@Michael Shaleesh, That's not the worst return in the world - especially since you're occupying two of the doors for personal use. 

@Beary Bowles none of the old time owners ever did a tear off on the flat roofs, so now when I look to buy a building with a flat roof I always expect a worst case scenario.

The housing collapse from a decade ago, people thought was the worst recession since the great depression, but completely gloss over the early 80s recession where unemployment reached higher levels, and without the kind of social safety net we had in 2008.