Once you've identified what's important and what ratios to look for to evaluate a property, all future deals should be weighted against those "good" ratios/numbers - and periodically adjust to suit your goals.

I am now working with a realtor and she is saying we could sell it around $380k.

Quote from @Lee Loen: Hi,I'm an investor looking to acquire land, build, and sell luxury homes in the Scottsdale/PV area. 

I think you would be wise to sell and use the VA loan for your new home. 

If your agent’s estimate of $280k is accurate, this could be a good time to sell.

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. 

My advice is generally: seldom sell. 

Quote from @John McPherson: Looking for tips on the best way to sell my Rented Homes in 1 transaction .

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

How do you identify emerging markets before they become over saturated?