It's pretty common for lenders to have that requirement of >20% equity owners.

If they took the deed with "joint ownership" as opposed to "owners in common", then the surviving owner inherits the property and it doesn't go to other heirs through any sort of probate process.

In order to understand the cap rate, you can do some research, which  might include: 1) Looking at recent broker reports to see where cap rates are in your area, 2) Call a few brokers about current offerings in your areas and see where cap rates are currently, 3) Call a few banks and inquiry about their refinance options as well as where cap rates are, 4) Ask a few property managers in the area.

In other words, they want you to be an investor, but still have a 9-5 job just in case all of your tenants leave and you need to pay the mortgage (as if that's a common occurrence). 

Use this as motivation to start creating a troubleshooting manual for common problems in a rental.

Hey Joey, this is definitely a common feeling and it sounds like you've already done a great job of getting started.

I have found partnering with others allows me to continue buying good deals.Research "Tenants in Common" as a way to partner on deals.I am open to discussing my success with getting my investment money out of a deal or how I am working with partners. 

As if it's common knowledge, which it is not. 

Finally, in situations like this, where Bob is taking the loan solely, is a common selling point to Bob the ability to do the same thing as I mentioned before with taxes in order to offset his DTI based upon the income the property produces?

Upon expressing interest, we email them a tenant profile and that eliminates about 95% of the inquiries.