Please don't take this the wrong way.... this sounds to me like a rant of a spoiled child.  

The kind of person who is always found on the sidelines, never in the game, terrified of putting a foot wrong because he spends his whole life running from risk and sneering at anyone who actually tries to do anything useful.You should worry more about being those things than bring broke.

Surely the insurance carrier would put there foot down and cancel the policy, which would force the home I to default being uninsured and no one to pick it up?

Could be someone died and left it to a child that lives really far away and doesn't want the property.

As of July 1st, new tenants have moved in, a young family with one child; while my father occupies and pays a small rent (previous arrangement) for the downstairs room and bathroom.

You already have your foot in the door because it wasn't a "No".

Have to time it with replacing enough of our w-2 income with rental income to make the move feasible/not shoot ourselves in the foot from a financing standpoint.

Apartments- New kitchen layout, moved laundry into each unit, updated bathrooms, new windows (curb appeal), updated paint and flooring, turned the laundry room into the 12 unit.AirBNB- changed usage on the main level from office to 2 unit AirBNB.Office building- removed drop ceilings to add 3 foot ceiling height to make the space seem larger with more natural light.

I will take any advice I can get.I am here to learn and if that means I'm doing the work no one else wants to do to get my foot in the door that's what I'll do. 

(I’m currently active duty Marine Corps, we are about to have our first child in less than a month and my wife plans on working shortly after our son arrives)-Should we raise the rent on the inherited tenant?