The house is a sturdy 2b/1ba that is renting for $550/month - if I put $5K put into the property I'm confident and the numbers prove I could be getting $300+ more dollars a month.

That means that the title examiner has total confidence that the chain of title is completely clean. 

Still, these are my loans of choice because of the time and headache factor... and closing confidence.

Once you can navigate that successfully you will have more confidence and experience that is needed to do larger riskier project.

I felt confident, educated, and well positioned mentally & financially to acquire a property. 

Based on the candidates you've presented, I personally don't feel very confident in their qualifications and would wait for more to apply.  

It is about knowing your numbers so well you are confident in the deal.

I can confidently say it is worth it for a Buy n Hold investment!

You're very confident that my opinion is worthless; what's the cutoff age for having an informed opinion?

Here are some of the resources that I don’t see mentioned too often that really helped me start with confidence and that made me money(or saved me from losing it) on my early deals while I was gaining experience:*The first 150 episodes of the BiggerPockets podcast.