Depending on when I buy the house- thinking next summer- I may not have 20% saved up, and it is a possibility that my parents may be able to give me several thousand dollars to make up the difference on the down payment, and I would not charge them rent for the number of months that corresponds to the amount they give me ÷ rent. 

If it were summer, you could pull the A/C disconnect.

My husband and I are starting to look for a second (summer) home in Durango, CO, and would love to find something we can rent out as a vacation rental when we are not using ourselves.

They dropped the price this summer by about $500k, I'd still like to offer significantly less than asking.  

The prices change from winter months to the summer months due to the demand of places to stay during the snowy months.The way that I Calculate the potential monthly income for the property is somewhat complicated.

Regarding the Student Housing issue, I just rented my only open rental already for next summer and next school year.

Houses sell the best during the spring and early summer months and travel/tourism is pretty good year round but much better in the non-100 degree months.Since you're going to the midwest, properties are considerably cheaper and cashing out here can probably get you a few rental properties you can self-manage once you move.

The Military gave me my last paycheck on the first of November but will start giving me housing allowance for attending school every semester (they don’t give me allowance in the summer or between semesters).

In the summer, I'm guessing you also have to cut the lawn and that should be factored in as well. 

I put together a personal financial statement together today and if I live on beans and rice for the next few months, I should be able to save about $10,000 for a down payment this summer.