I've been told by their support team that they'll be adding automatic payments for rent in the next couple of months.

Quickbooks for the business, mint and personal capital for overall pictures and mint bills for all of the bills and due dates in one place.All are free but you will be added to marketing for their offerings. 

As a single family you should discuss with the agent to see if the Insurance Carrier will accept it and also what, if any, endorsements need to be added to the Homeowners form for the rental exposure.If you do have to go the Landlord policy (Dwelling.Fire or DP3 form) you may also need to have Renters Insurance for your belongings and Loss of Use.

What should I require to make sure the son is in fact a minor or should be added to the lease?

If your goal is financial freedom to obtain as much rental income + tax benefits as possible - you may want to consider keeping it 100% a rental and just rent out a different home when you want to visit the area in question.Please also be mindful that the cost that you pay to purchase the land and build on it will be added to the basis of the property and depreciated(possibly prorated if vacation home) over its useful life.

I am currently trying out Stessa, but it feels more like a "financial" and doc storage software.I currently self-manage and will be adding an executive assistant to take over this role.

My cashflow on this property is $3,830 and my new appraisal value is $995,000 = Equity built in 2 years $497,000Obviously I'm leaving a lot out and will answer any questions about these 2 projects and will be adding pictures from these projects too.My new current project is a 0% down VA new construction owner occupied quad-plex buildThis will be my first new construction. 

This includes maintenance, vacancy, loss to lease, management, taxes, payroll, contract services, utilities, admin, ect.CapEx expenses should be added back into NOI. 

I'd love to be added to your buyers list as you start finding deals!  

How can it be added to property?