Nice.
Point 1 can't really be addressed without addressing point 2 first because, as you say, you would miss messages. If you know that person P posts on relays (X, Y, Z), you can ask 2 relays (X, Z) for those notes and because they both should have them, it's usually good enough. If not, ask on 3 relays.
If you instead ask the user-configured relays for P's posts, then asking only 2 of those relays is probably going to miss tons of messages. But even if you ask all of the user-configured relays, you will both miss many messages and will also download a lot of duplicate data. The only way to get all the messages of all the people followed (and avoid excessive duplicate downloading) is to go out there to that unloved relay in Timbuktu that the user didn't configure (but that P has in his relay list) and fetch them from where P wrote them.
Of course, fetching from relays that the user didn't configure has implications.