So I've made the decision to focus on getting Hannah to sleep at night on her own and putting the naps on hold for the moment. She settled herself in 10 minutes tonight (yay!). Hopefully its the progressive-waiting approach working rather than the over tiredness from sleeping a mere 1h45 since 9am.
As for the naps, as much as I hate it, I will rely on the car seat, stroller and boob (sleep associations) for now. I'll take the 10+ hours at night for the moment. Definitely an accomplishment in the past week.
One step at a time...baby steps you might say.