I am also in the same boat, and just getting entry into buy and hold in NOVA is very expensive.I think Prince William County (Manassas, Woodbridge) would be decent but cannot be compared to Richmond, VA.

Is anyone else in the same boat or was in the same boat and figure out the best way to go about this in order to shelter most of these gains -especially for a single person? 

Yup, I'm in the same boat as you! 

I am currently in the same boat.

Investors who plan to hold for the intermediate to long term miss the boat by concentrating on buying a property “below market” to the exclusion of all other criteria.  

Even if you have capital and a boat load of experience - you're gonna get smoked at least once! 

I may also being taking this too literally and to the extreme, but as a Landlord in CT I don't recommend rocking the boat or getting on the "bad side" of any housing regulations.However, if you own the property and live there yourself, then no.

If you are insurable, have a significnt financial risk of premature death, debts, kids, obligations, get some life insurance, most people are in that boat...not just a risk now, but the likelyhood in the future as well.

Hi @Jamie ShahFollowing this post now as I'm in the same boat today, checking to see if you have invested in Tracy?

Although I do not have any advice that may help jump start you, I just thought I would welcome you to BP and let you know that someone a few states away is in the same boat you are.