Hi Matt,
How are the utilities set up? It seems to be light. Is the property on oil or electric? separate meters? shared boiler/furnace? As a comparison, I budget $475 in a duplex I owner occupy in Anchorage (water and gas are shared).
Insurance: You are probably $75-$100 higher than you'll get when you owner occupy.
Maintenance: snow removal should be included under this item.
Appliances and other unknown rehab: I had a fridge go out within a month or two, consider buying a home warranty with the purchase. In retrospect I wish I had - there's a lot of advantages about them when you read up on it.
Buyer paid closing costs: Are you splitting? is the seller paying these?
PMI: VA loans do not require this, but anytime there is less than 20% LTV, it should be considered in the analysis somehow...
Reserve funds: I don't qualify for VA, but for AHFC they require 6 months PITI. Do you have this much? It can be risky when your reserves are too low right after a purchase.
3 month vacancy: Have you considered doing a vacation rental (AirBNB) to cover the gap?