Now, I have a "nanny" (handyman) looking after all my babies and I just check in to make sure they are performing at peak..

If I switch to something like ring, and just have a camera on the outside and a video doorbell.

Any recommendations for 4-5 cameras around a SFR, preferably ~$200, that can connect to my phone?

I'm thinking of a way to set this up, instead of having to hire out someone to do the showings.One thought was to potentially set up a security camera system. 

Best way to confirm status of Cast Iron Pipes is to have a plumber run a camera down the line to look for breaks / failures.

That is terrible advice and, obviously, the people who take that advice fail catastrophically because, as it turns out, brides don't really want you to be learning how to use your camera on their wedding day.

Did your contractor inspected the pipes with a camera and looked at the septic tank? 

I got a plumbing company to come snake it out and they did a camera view and saw that the connection from PVC to the City Drain has a short clay pipe still there...thus with the ground shifting the PVC no longer drains clear to the City Drain.

She is completely aware that i have a doorbell camera as well as a indoor camera inside the kitchen facing the living room. 

@Jess McLaughlin would still want liability, business income, wrongful auction/towing/gates/cameras, etc.