Hypothetical Quandary of the Day – Mega Millions Tax Shelter

Like most of you, I awoke on Wednesday to a sad revelation: I did not win the Mega Millions jackpot. Being the Lord of Petworth does not pay as well as you might imagine. Even I could use a few hundred million.

But let’s just imagine, for a few moments, that you had won.

What would your first thought be? Taking care of relatives? Feeding the huddled masses? Hell no. You’d be thinking about tax shelters.

Let’s say you were at a meeting with your financial team (being filthy rich, you’d now have a financial team) and they’d come up with a brilliant tax shelter that would let you make a substantial investment in a Washington, DC, neighborhood, as well as protect a good portion of your undeserved new wealth.

The shelter would require you to invest $15-20 million in a neighborhood development project. You would select currently vacant buildings, renovate them, and start businesses in them.

There are some rules:

(1) You must create something where there is currently nothing. You cannot displace a current business or residence. It must be an empty space and new business (or businesses).
(2) It must be a commercially viable for-profit business. No renovating buildings for a youth center, homeless shelter, or senior center.
(3) The business must realistically be self-sufficient and begin turning a profit within five years.
(4) You must make the case that the use of this space will improve the quality of life for the current residents in the neighborhood you invest in (no opening yoga studios hoping that gentrifiers will eventually move to the block).

So, okay moneybags. Your check-writing hand is getting itchy and your financial team needs your decision right now.

Where do the millions go and what do you put there?