I'm aiming for the 10 "easy" loans, and then will move on to other products.

The direction you start doesn't have to be the ultimate direction you go in but you have to aim somewhere.

Whether purchased with four different loans or with one loan across all properties, the loan to value measurement will be a key factor in whether you can take money out.In your case, if you bought in a market that appreciated, you may have more value now than when you purchased, but probably unlikely.  

Grades and degrees are not a measure of intelligence (within reason), they are a measure of effort.

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.