1. Feasible, probably.
1a. Also feasible. Of course, the NF problem still contributed to timing and stuff for the heart of the city plan. Could possibly throw things off anyway? Make that definitely, since DOS head guy is the right hand man of Bedlam, and is involved in getting the map too.
2. Just get him to stop emailing Penelope with frequent updates and pictures on how the map is going, honestly. The DOS knew when it was about done because of that. (Dave doesn't know it's a map, he thinks it's a logo requested by the Lucid Corporation.)
And you'll have to stop him from getting kidnapped too.
3. I'm not sure that's feasible. Bedlam clearly isn't omniscient, but the Sideways are her territory, even if she can't find the heart for some reason.
(edited)