Should I sell and do a 1031 or refinance?

[Brandon Koon]

I am trying to decide if I should sell my rental or keep it and refinance it?  Here are the details of the property.  It's a twin home that I bought 9 years ago.  It is currently cash flowing $300/month.  If I were to refinance it, the cashflow would go to $680/month.  And if I do a cash out refi, pulling out about $15,000 the cashflow would be $540/month.  Or I can sell it and have about $65,000 to use as a down payment for another rental.

I am really struggling on what to do, because almost every investor that I have heard says the one thing that they wish they would have done different was not sell anything and buy more.  So I am not sure if I should just hold on to this forever and keep it for the cashflow.  Or sell it and try to "upgrade" to something bigger/better.  The problem with selling it is finding a deal within the 45 days allowed for a 1031 exchange.  And if I can find a deal it will most likely be cashflowing less per month than what I would be getting if I refinanced it. 

I know there is no right answer, or one size fits all.  But I am looking for opinions from other investors that have been down this road.  Do you wish you would have never sold a property?  Or are you glad you did, so that you could buy another one?