Just make sure you have proper locks on all access doors to avoid theft disputes between the tenants. 

Solid path to enter the multi family space.

I'm trying to decide what to do with the second house in terms of leveraging the space.

Not ideal mind you, no windows, only access would be through the garage (although the tenant would also get a garage), the only access I'd have to "my" side of the garage would be through the outside, etc.

We also caught a lot of lucky breaks along the way like: a very friendly banker, access to private loans from partners and family, baby booms looking to move out of state and off load property at cost.

@Justin Frye If you're an investor that is looking to grow your portfolio I'd recommend calling the smallest 5-10 banks and/or credit unions in your market.The portfolio lending arena is much more flexible than the conventional space in my experience.

@Andrew Harwell FEMA has a flood map that is accessible to the public and so do most city websites.

Landlord shall provide a key to the Tenant for the Premises and Landlord shall keep a duplicate key for access.

I know I'm not responsible for it, but I'm a bit puzzled by the solution as the hole is large and there needs to be space for two pipes to fit through. 

There's a small house towards front of the lot that can be renovated and rented out, I'm wondering about dropping in tiny homes or renting out space for something else.