Get a professionally written lease, start screening potential tenants. 

I'm a broker, not an attorney, so seek professional legal advice.

Read the HOA CC&R's.As always, don't trust the internet, seek professional advice.

I would suggest developing relationships with realtors and other professionals in you area to source properties before they become public. 

PM failed to follow through the full eviction process.The PM is not a professional and you should fire them.

I am now ready to move forward in this business, or close to it so how do I present it to him so that I can make him feel at ease with my professional analysis?

I have had great success with French Drains (google) I had a property in Ca and sometimes it rains furiously there and water would literally pour into the basement like someone turned a tap.

The company is currently using are less than professional, they seemed to have forgotten to collect debt on one of my units last month.

You'll need to run sprinklers throughout the house (costly for a number of reasons, especially if you have to increase the water main size), have an enclosed trash area with a drain, have electrical exist signs at the egress points in the house, and they will ultimately require you to become ADA compliant.

Having it allows me to not only to buy, sell and pay myself but it helps us on our taxes since we are investors (ask your CPA about being a "real estate professional"), allows us to view homes when we want, I can lease property in my state and it allows me to be a property manager.