Additional costs will creep in and costs seem to go up faster than rents, so I would sell and try to otherwise optimize the VA loan. 

Your primary residence - if you've lived in it for 2 out of the 5 years prior to selling you'll get the $250K/$500K tax free iike @Clint Galliano said. 

Long-Term takes the least amount of time, Short-Term the most.Unless you have the time & discipline for this, SELL.4) If you sell, would it make sense for you to re-invest in other rental properties?

FWIW, I would sell the Houston primary for sure.

Selling vacant is easier, but if you can't/don't want to vacate the property investors will still look at tenant occupied homes 

Hello, I am looking to sell my rental property in Toledo, Ohio.

Is it safer to find a property already occupied? 

Also, if you have a below market interest note, if you wanted to sell that note for any reason in the future for liquidity you would be affecting the value of that note negatively.

Tyler local, so sparked my interest whenever I see anyone post about the area.Given that your duplex is fully paid off and generating a steady cash flow of $1400 per month, it's understandable that you're having second thoughts about selling it.

Other Strategies: Are there safer or more profitable alternatives I should consider?