Keep rental or sell for primary residence tax-free profits?

[Brandon Borah]

Hello BiggerPockets Family!

I have a home in Fishers, IN, which is a pretty hot market for rentals, but even more so for selling. I currently have a rental with a PITI of $591/mo and projected rents of $1,350/mo (tenant moves out on 4/30/16). I owe ~$95K and could sell if for $170K with approximately $10K being put into it (so ~$45K to $50K profit when all said and done with commissions and additional costs).

I lived in this home for 2 of the past 5 years, so I would be excluded from the capital gains tax, which is now why I'm in debate of holding this as a long-term buy and hold strategy or sell and reinvest the profits into other properties. 

I currently live in another ranch in Fishers with two roommates who are renting rooms from me, but would like to eventually turn this home into a rental as well. If I sold the investment property, I would be able to sell my current primary residence in two years and get the same tax free exemptions, even it has become a rental (so essentially repeat the process from above). 

My question is based on your experiences, is it better to cash out and sell or hold for the future? Based on what I've seen, most people swing one side or the other, but was curious to see if any one has used a strategy similar to the one I am presenting above. 

I appreciate your input!