Love the concept, I don't know what I did wrong but it felt like I just kept getting contracts and Betty never came back after the second time. Something from Barry telegraphing what actions might trigger more of the interior decorating side of the game and/or which days are more likely to result in visits would alleviate that.
Also had one case where the mark spent the entire assassination mission just offscreen in the areas you can only see when you're aiming - if the existence of them isn't a bug, then having a mark just never leave them probably is.