It sounds like you're about to tackle that project and I would wager that the air infiltration will be greatly reduced or eliminated once you insulate the attic.

I would wager that it's an incredibly high probability that it doesn't happen today for anyone except the most inept and incompetent lender in the world that doesn't plan on being in business in six months.

All that work just to have less cash in your pocket in the end...people typically wager that their rental profits will exceed the difference between their purchase price and their sale price (after paying any closing costs).  10 years might be the problem with your calculation.  

But I figured I had some room to wager with cash considering the listing price is low and the surrounding units vavancy.

I'd wager you could find the appropriate meaning seeing how badly you want this to stay on topic...

Now I am getting notices from my HOA and thinking about strategies.I am thinking about selling this property and taking the equity and parlaying it into a 8+ unit multi family property.

Would allow me to stay in this nice updated house with my dogs and use the extra cash to parlay with private money to do this all over again just on the side.  

In fact, I'd guess that it won't, I'd wager that it won't, and if I thought it would I'd probably have my properties on the market.  

I don't quite have the experience to wager my personal house on one deal.  

Because of this I would parlay that into my brokerage account to buy more dividend paying stocks and increase my income.