To move or not to move?

[Lauren Daly]

I have a dilemma that I am having a hard time getting my head around. I'm guessing I'm not seeing all the angles.

My fiancé and I are buying a house for $140,000 and we are going to try to put 3.5% down if we can get it approved (we have the cash to do a larger down payment but would like to reserve it to redo the flooring and a few repairs, all of which are not immediately necessary). With the expenses factored in, we think the property will cash flow $200 per month. 

Currently we own and live in a condo which we have always intended to rent "one day" when we were ready for a house. The condo is in a community which comes with a whopping $400 HOA and country club dues fee. The property would cash flow $-37 per month if we rented it.

We need to decide whether we are going to move into the house - which would decrease our current living expenses by ~$500 per month because the tenant would be paying the HOA and club dues, and we wouldn't pay inflated club prices just for convenience- or stay in the condo, and take our $200 cash flow from the house? Any guidance?