When you say 40% annualized is that per year or over the entire life cycle.  

They are rules of thumb we use to function day to day because the FACTS are too needlessly complicated to use to make every decision in life.

It's about having an income that will enable you to maintain your current standard of living for life.

The seller is not very tech savvy and is going through some life issues so he isn't being very helpful in this.

First off, congrats on the soon-to-be dad's life—huge milestone right there!

We started looking at coaching programs and some of these things just seem ridiculous at 20-40 grand, and some seem more like life coaching programs as opposed to real estate programs. we don't want to syndicate we really would just like to find someone that we can bounce deals / ideas off of and have them assist in underwriting and giving us a better sense of security that we are doing the right thing.

Even in my life.

I have a Indexed Universal Life policy that is 7 years old.

What's the life expectancy of the roof, paint, furnaces, water heaters, etc.?

Even just adding an extra $100-150/month to the principle can take years off the life of your mortgage.