Red head moment!

That way you don't go one day in the red. 

@Jack Mitcham Welcome.A lot of Red Sox fans do this also: Go to games in Baltimore because it's cheaper;-)Good to see you're persistence in hanging on is paying off.

I'm pretty rookie myself but from talking with others, the market here is good but not "red hot."

Letting the selling side know that you can close in 2-5 days because you are closing HARD with cash makes you stand out among the rest of the investors that has a lot of RED TAPE on the contract.Hope this helps

Are there any other red flags that I should consider regardless of him accepting my offer?

She was probably about sixteen when she was arrested eight years ago, so I don't see a lot of red flags, but I still find myself wanting to turn her away because of it.  

Also another red flag is if they currently have no inventory at the time of your conversation.

However, there are some Red flags in the listing, it says it can be a duplex, which means it does not have 2 units on the property and the house can be added to to make it a duplex. plus it also says the buyer is responsible for certification and repairs, it may need more repairs then what is in the pictures plus again that seems to mean that the units are not safe to rent and not legal to rent and will have to be certified as such.

This immediately raised red flags but I found no point in pushing it if they were going to be out one week later.