Advice on Renting my Property or Selling it? Pros and Cons

[Evan Griffin]

Hi, I live in Redmond, OR and will be moving to Eugene, OR April 2020. I have time in my favor and I'm trying to make the best financial decision. I work in Alaska 8 months a year commercial fishing and am on my second property. 

I currently owe 280k on a 3 bed 2 bath 1750 sqft home. I can sell it between 330-360k as of today. Working out of town I will need a property manager (180$) and I'm 200$ short on my mortgage for what I can charge to rent. 

Total 380$ in the hole besides all the things that can occur being a landlord. 

Is Appreciation and paying down the debt of the loan worth taking that monthly loss if I can afford it?

Central Oregon is a highly desirable place and I'm located in a great neighborhood. 

(mortgage payment will drop 200$ after 20% equity automatically)

Or do I sell the property and hold on to the money until I find a good buy in Eugene, OR? 

Im new here. Any suggestions or advice would help! A lot of my knowledge is reading at sea and the experience of purchasing two homes. I am 26 years old and long way to go! 

Thanks,

Evan Griffin