All of this is a bunch of red flags... we're worried she lost out on her next place and is planning on staying longer, without the lease or security deposit.

(Sorry I missed this last month, not sure why it didn't flag as needing response for me.)

Red flag.

I tried going through several brokers (Young Alfred, QuickInsured) but none of them were able to find a carrier that allows for my situation. 

We can then measure the gap between where you are and the banks minimums and have an idea of a % of savings that could possibly be had.Step #2 would be to remarket your account with those minimum requirements and see if anyone in the market can beat your incumbent carrier.   

I am not looking to rent to either of these applicants since I have other options and there's a fair few red flags flying with both, but it's made me realize I need to add a couple of things to my criteria for the future.

If the paint doesn’t match 100% to the original, will this get flagged?

BP released a market update recently discussing yellow flags in certain markets so that may be of interest to you to listen to. 

We were only attracting applicants with issues and red flags because it was too high for the higher quality tenants. 

Big red flag.