If you have the option to buy a $1,000 pair of shoes or house. 

In November of 2014 we had the wife of a husband-wife tenant pair inform our property manager she would be moving out.

If the traditional STR markets aren't taking this (Foremost & Proper), I would suggest connecting with an independent agent and they can try the following,1)  Try and find a carrier who can pair the high risk property with your Home and Auto policy.   2)  Find a policy with a Lloyds of London type insurance carrier3)  State back insurance - Each state has a Property insurance fund as a resource if the public can not find coverage. 

Most people like to enjoy some sort of holiday meal and/or HAVE TO buy food and this would pair well with the timeframe you're wanting to give something back. 

I was counting on the FHA loan, paired with down payment assistance to fund this property so I could take advantage of being a 1st time home buyer.

I own several “pairs” of properties on the same street with identical sf and build dates with very different taxes. 

Tell your loan originator/lender or mortgage broker you would like to use purchase property income to help you qualify and they will pair you with the best financing package that does what you need.

I'm currently into a pair of single family homes on a single plot (zoned like a duplex) for an unholy $490k but the gross rents are going to be $3,400/month.  

You could also rent out as a whole unit but include a slight increase to rent if that unit is going to have a pair of roommates living together.

Why not pair up initially with a Realtor in that knows the area that you're wanting to invest in and leverage their access to the MLS while you start getting your plan worked out and consistent money coming in?