This is all sorts of wrong.My initial issue with Matthew's advice is that the property has only been owned for a month so unless the "wind damage" occurred during that time there is no covered loss here. 

Eventually I would like to set up some sort of "in-house" property management to cut back on these fees.If you are able to self-manage those rentals, though, then the fee is a non-issue!

So, if you want to build on any sort of schedule you will be left with D and F contractors. 

What sort of investments are you planning... fix and flip, buy and hold, etc.?

The options were  keep doing what I was doing and try to save my way to wealth (which really doesn't work on any sort of timeline that I found acceptable) or take on risk in as careful a manner as possible and go for more.  

Everything going through my mind is around securing our income during retirement and leaving some sort of inheritance to my children. 

Is there any way to file a change of use permit of some sort that would make this business model work? 

In exchange, I’d be able to be sort of an intern or someone to help with boots on the ground here in AZ.  

Buy or inherit and hold all their lives while working the properties for income.I've seen teachers, firemen, software engineers and all sorts of people utilize both strategies successfully.

Their main goal is maintaining wealth not creating it, so they are diversifying through all sorts of different investments. 8% returns are on the high side.