Sell before it does.  

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?

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

FWIW, I would sell the Houston primary for sure.

My advice is generally: seldom sell. 

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

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.

Planning to sell my property in vegas, just wanted a second opinion on if these are typical, fair costs in today's market.