If at the end of the day, all "pieces of the puzzle" align, then I'd consider moving forward with the investment. 

This is quite puzzling to me and I was wondering why people do it.People often let cash sit around waiting for the home run deal that only comes along every few years instead of having it in play in good projects consistently.

There's a lot that factors that go into conversion rates - your site is only one piece of the puzzle.

The other piece of the puzzle of course is your Property Coverage, which has its own nuances, but covers the actual building itself.

So, look at the experience and short time you had with him as just another super tiny piece to the puzzle. 

So we have a ten unit complex and have owned it for four years.  It's a great solid building but the main issue has always come down to water usage.  In the last two years, during the same winter months of Nov/dec/jan...

What am I missing in this puzzle?

I know that's only one piece to the puzzle. 

Many ideas going through my head and I’m looking for all the pieces of the puzzle to put it together right and get started.

Finding enough funding and deal flow is the second piece of that puzzle.