I use a separate bank account for each property, so my bank statements become my profit and loss documents.

you have to be positive that the numbers will yield profit for all involved parties. if you aren't sure of the exit strategy or how you will secure funds then you still have a far way to go. do you have cash buyers with verifiable proof of funds lined up?

Done several dozens flips, and owned a 4-plex that was purchased for $68,000, cashflowed almost $2,400 per month, and sold for a $100,000 profit less than 3 years later.

The organization is (as best I can tell ) a non-profit run by lawyers that sue insurance companies so they are biased to the homeowner, which for you is good.https://www.uphelp.org/blog/north-bay-fires-insura...2.

They tend to care more about an A plus location then the cost per sq ft in rent as they believe the location will drive higher sales.Regional to mom and pop tenants are more sensitive to being in a high end area but not the most expensive center or corner where they feel they have to drive very high sales to have a chance of being profitable.

(I assume this would be another loan, which would be pointless to borrow against your own profits, basically depreciating the appreciated profits by borrowing against it).

In general the best (most profitable) angle, although the most difficult, is to sell the totality of units as a package... which requires everyone to be on board to sell.

Once I get it to that point I can just sell it as is and make my profit, or I can add a 3rd bedroom and a living room to the house and make it a 3 bed 2 bath(1494 sq ft) instead  of a 2 bed 2 bath (1028 sq ft).

So if you are flipping the home, they will analyze each property to make sure you can sell it at a profit. 

The land is definitely not worth $150k and the owner would stand to profit off of this deal more than anyone.