However, due to the whole area now being deemed by insurance companies as a "fire-risk" zone, I can't find a single insurance company to put a STR endorsement on a regular home owner policy up there.

Their guarantee to cover the mortgage if they don't rent the property is a red flag, too.

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.

**Ethical Concerns:** At the time I joined, certain marketing tactics raised red flags for me.

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. 

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.

The fact that you've "put over 5 offers on houses since February" and moved to a different strategy is a huge red flag for me.