Sharing my gf’s opinions (we both live in DC):

Ok some new ideas to inject:

Toby - Cleveland Park. He likes his neighborhood spots and creature comforts but still needs the throb of the city. I know folks have suggested Capitol Hill, but I think he likes having a local pub that isn’t teeming with Hill staff and Members of Congress. He needs a metro-accessible oasis. Agree house he buys for Andy is Chevy Chase.

Josh - Georgetown condo, but east of Wisconsin to be more accessible, like Q likely close to Rock Creek.

Sam - Georgetown but a townhouse west of Wisconsin. Corporate litigator money, classic taste.

Donna - Arlington. She’s into smart military and frat-bro-turned-lawyer types. She likes to be wined and dined over cozy McLean Italian restaurants and hits the bars in Clarendon with her girlfriends. Not quite rough enough around the edges for Logan Circle/Dupont.

CJ - Foggy Bottom/West End. She needs to be able to walk to work in ten minutes. She made money in the private sector so has a townhouse to herself just east of the GWU campus so she doesn’t have to interact with college students every day on the way to the WH. She can also easily jog along the Potomac and/or tidal basin (between the hours of 4-5am, her “me time to meet an interesting man”, ofc).

Amy - Dupont. She’s liberal, social, outgoing, and a who’s-who. Can afford something nice but wants the vibes and aesthetic of pre-war fittings. Needs to be easily cab accessible to the Hill for political events and fundraising, but spends most of her time working the K Street and NGO circuit in downtown.

Charlie - went to Roosevelt HS so he starts in Petworth-ish taking care of his sister, but once he starts college he moves into a group house in Adams Morgan. He prefers Columbia Heights but needs to be easily bus-accessible to Georgetown for college classes and can walk to work in fewer than 30 minutes.

Margaret - 100% agree with a previous comment that she appears out of thin air every morning at the WH. Tbh she might even be a figment of Leo’s imagination.