As always, don't trust the internet, seek professional advice. https://www.hud.gov/sites/documents/SERVANIMALS_NTCFHEO2013-01.PDF

The frames are rotted, the lintels look like they've popped the stones/masonry and letting water through, and there's some sagging of the front porch (above these windows) causing a few cracks in the cement and more leaking into basement room below.

Much like "any" professional you are bound to get different answers, including out here.

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. 

I set up multiple reports that give me an updated task list every day so that important events don't fall through the cracks.

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?