3- Feel free to tag someone who is well versed in DC zoning here whether this person is an agent or a lawyer. 

I don't have any pending legal issues at the moment, but I've been thinking I should find a lawyer that I can go to for questions, to review documents, leases, etc so that I can have confidence that I'm not making any silly mistakes that will get me into trouble later on.

Otherwise, you could also provide prevention recommendations somewhere on the lease that includes what you've mentioned above.Assuming you don't have a lawyer to help with your rental agreement you can find some sample clauses on a site such as Law Insider.

Anyways I sent him a notice through a lawyer about this issue stating that he is breaking the lease.

Quote from @V.G Jason: I'd partner with a lawyer that can help put some contractual language on the downside of working with contractors and real estate agents.I'd also partner with a RE brokerage firm that clearly understands your goals. 

Obviously speak to a lawyer or someone with more knowledge, but I have heard of people leaving their FHA home before the first year is up for much worse reasons. 

I don’t believe a tenant can stay forever, and I can cover the extra payments and lawyer fees for up to two years for the tenant who will be harder to remove.

Practiced as a lawyer and also had various investments.

I had a conversation with a Probate/Estate lawyer and he suggested the following but what he said doesn't quite add up to what I have read so I want to see if I am just not understanding or if I am getting bad gouge.Advice was to create WY LLC that owns all properties, that is then "owned" by a land trust for additional anonymity, that the beneficiary is a regular Trust that owns everything else in my name.

In many states, approved sales contracts are available for free online (you'll have to learn how to fill them out or pay a lawyer to do it, recommended to at least have a lawyer review).