Another post-tenant property had multiple holes in the walls and the entire tub/shower insert was falling out.  

My worst fears were realized when we found there was a big hole in the roof, and over $10,000 in damage to the property.

Several months ago I found "The Book on Rental Property Investing," and began to see the holes in my business. 

But outside of these logistical issues, is there any gaping hole in my logic as to why this would be a bad idea?

Otherwise you have a big gaping hole that allows the elements in.This summer I have had 4 swamp cooler related phone calls that required rapid response. 

We had a rodent problem in the attic area that was dealt with and outside holes were blocked.

I changed a water heater, huge leak in one of the units, electrical issues, and I even had to dig a 3 foot hole under the house and personally fix a pipe.

Trapezoids can fit in square holes, but big box banks are only for squares in square holes.

Make sure door sweeps are on external doors, make sure there are no gaps round the doors, make sure all holes eg plumbing fixtures under sinks are sealed, pipes going through walls are foamed up to seal, and so forth.

In any case, my study has still left these holes, so just looking for insight.Thanks all,JTM