Thanks again everyone!
After a few reads I'm finally starting to understand a bit more (especially the abbreviations lol).
So correct me if I'm wrong here. I should do something like this:
1) Pull my credit score
2) Apply for the Chase Freedom Card (if denied I need to get revolving credit somehow for 6 months by going with an easier to get student card)
3) After a while with that card get the Chase Sapphire Preferred when they have a big sign up bonus
4) This will transfer points from both Chase cards to UltimateRewards
5) Convert UltimateRewards to Amtrak points/tickets
Hopefully I got that right
Thanks for your patience.