Outdoor storage, moving services, additional parking.

This initial negative equity position consumes the initial cash flow.  2) the addition of the adu makes the property multi family and likely makes rent control apply.  

I have about $100k in capital reserves and can leverage the 2 properties for additional capital, as needed.

That would be a helpful addition to your plan as you would further reduce your cost of living.Also don’t forget from that $600 you are planning on getting in cash flow you have taxes, insurance, maintenance, capex, and vacancy to consider.With two homes, you may want to keep that extra $20k as an emergency fund rather than spending it on a third property and then be left with no emergency funds.

What would be my best route to take if we need additional finances?

All this in addition to 6 other lease violations... 

Quote from @Lisa Albright: Hi All,Newbie here, just a quick question we are building an addition on our second home, we have a primary residence, and two rental properties.

Additionally, I really want to dive into the property management realm and am passionate about connecting and assisting other Veterans and Active Duty. 

Your best route might be to buy a 2 to 4 unit property that you can live in and rent out the additional apartments.

Principal balance currently at 314kProperty Details: It's essentially a "2-in-1" property, with the main unit rented out for $1,900/month and an attached ADU bringing in an additional $1,200/month.