Hello JC,I am not an expert in DC specific zoning but I have a lot of experience with the zoning code in Charlottesville VA. 

If the number are close[100k or less], do preemptive due diligence [water, sewer, stormwater, planning and zoning] if the property is considered for a new build development situation.

When developing, I'd first talk with the city building/zoning about what they want to see more of and where, and try a simple project that should be smooth sailing on plan approvals, saving you time and money. 

It gives you the flexibility to get started quickly and stay on track without the red tape.

@Najeh Davenport  Start with the local zoning office. 

Quote from @Bruce Woodruff: Quote from @Peter Mckernan:Up front (First Contact) Red Flags - 1) Everything should be in writing and very detailed 2) There should be a very specific Scope Of Work3) They should not ask for much upfront $$, certainly no more than 10% - if even that.

Are there specific zoning or structural challenges in Florida I should be aware of?

Criteria:6 months STR2 bd, 2 ba, Single Level House Furnished with yard, washer & dryer with A/C (inland not near coast)Pet Allowable 40 lb labodor 10 yrs, 40 lbs Red Heeler Mix and 6 lbs catNear VA Hospital, shops, grocery stores (at least 25 minutes commute)

The 1st red flag question he went over made me laugh.

I'm currently flipping and have found a person looking to sell two properties that are both within an opportunity zone in CT.