The companies opinion was he took all reasonable measures to protect the property so the company paid in full on his claim.

However, some banks have a very hard time with managing multiple transactions at a time but interview your bank well and measure their responses if you need 3 or 4 at once. 

In order to mitigate some of your perfectionism, why don't you start by 'flipping' property to yourself (BRRRR) in order to focus on getting comfortable with the process instead of the demands on yourself to measure success in short-term profit.

I am glad they're aiming high.  

I have bought one home aimed as a future long term rental investment that is currently my primary  residence. 

I would suggest investing more time into this yourself as you said you are in it for the long haul before aiming for the holy grail of agents we all want.

I take measurements (or close estimates) when I'm on site.  

I recently joined as a bigger pockets PRO in a proactive measure to make my dreams come true and start down the path to financial freedom.  

The first time we went to see the property we couldn't get into the one unit because the key was missing, so we were not able to physically measure. 

We aim for long term tenancies.