I also make sure we get on the same page by writing down our roles, responsibilities, and even how we’ll handle potential challenges or surprises.

Have you seen any strategies work well in Anacostia (or neighborhoods with similar challenges) other than flipping?

Challenges?

Flipping during a bear market or high-inflation period can present some unique challenges, but it’s still possible to profit if you approach it carefully.

Yes, the BRRRR (Buy, Rehab, Rent, Refinance, Repeat) strategy is still alive in Philadelphia, though some aspects have become more challenging in recent years due to shifts in market dynamics.If you’re considering BRRRR in Philadelphia, areas with recent or upcoming developments, like parts of West Philadelphia, Brewerytown, and sections of Northeast Philadelphia, can still present good opportunities, but base everything on section 8 rents to see if the DSCR and LTV makes sense

See post from jay hinrichs about using them and some of the challenges they may provide.

Challenges?

I belive the property will be a challenge to sell because, based on comps, its over priced. 

That's the case everywhere...and each region comes with its own set of challenges.

Your SOW, challenging projects, expensive stuff, can be tricky unless you have experience and an established team.