I would be very surprised if you can find something with two legitimate dwellings in an A or B neighborhood for less. 

If you are NOT in an X zone, you are likly in an AE zone and then the rates are a function of the BFE Base Flood Elevation and the lowest elevation of the dwelling. 

Anything that I should focus on from the start, or instant red flags that are show stoppers?

(1) My husband already pitched the idea to her about this, so I'll just have to tell her that he didn't discuss this with me and the answer is no (2) Definitely agree that we are emotionally attached to this "dwelling" and have to see it as a rental property and not our home (3) We will talk with her, but I don't know how to avoid the small talk about us, I don't want to give her very much information and want to deflect all of her questions about us.

You can of course simply go to MHA and say, hey these tenants are month to month and I want to raise their rent because they haven't had it raised in a while.....THey will most likely look at that....and then,, presto...instant additional cashflow.....and most likely the MHA will pay the extra amount...not the tenant.Easy Peasy

Instead of buying it and getting $30K in instant equity, I'll make about $10K in commission instead.

When the market slips, you are instantly upside down.

The ability to instantly automate and communicate with people allows us to manage this from anywhere. 

Hi,So I’m purchasing a single family dwelling currently 1850sf with a basement.

@Skyler Chaney,  Hello Skyler, I've been looking at plans for an unbuilt tri-plex which when completed is expected to offer cash flow of several thousand per month, instant equity of near 20%, and a Cash on Cash Return on investment of over 50% the first year.