Side note: if your HOA doesn't already have an attorney familiar with HOA law in your state and familiar with your CCRs you should work on that.

Thats what I thought, just wondered if something had changed that would make Overages easier and possibly a fruitful side income. 

Will the passive income we start receiving (once our vacant side is filled) help with getting our new home loan?

I live in the bay area and will be investing out of state (OOS), I know by reading in the forum that Midwest is the place to go, I originally planned to go to Indianapolis however the multi family houses that I encountered are on the older side as such will have a higher cost of maintenance, the realtor I am working with setup my automated search in the 46201, 203, 205 ranging in the $120 - 190K range. 

Not only will I rent out the other unit but also rent out the rooms on the side I will live on to girls around my age.

I also work part-time as a realtor and help a small real estate company on the side. 

The property is a side by side town home , 2 bed, 2 bath built in 1984 selling for 64k or 120k for both units and potential renting the property for 1k a month.

Some relevant details:Located in a small, rural community2 family, side by side unitsLow cost/high rent (2% rule applies) areaPotential risks include: limited tenant base, tenant issuesMy inclination is to sell and move on, as it will take significant time/capital to get it back in good, rentable condition.

I do a lot of flips and buy and holds in the western side of the state near Pittsburgh I really appreciate that Alex, thanks!!

My point is maybe it is not necessary to paint if the siding is in good condition.