Dammit, I need to stop reading language courses for other languages, it makes me want to learn them.
Lakota looks like a pretty good language, but I'm not sure I should set too many language goals. Some of my ancestors were Native Americans, but we aren't sure which tribe.
How hard would it be to learn Lakota? Are there any Native American languages that are easier to learn? I'm intrigued my them, but know very little about them. And don't tell me one language is easier than another, because that is utter bullcrap.
You can't deny that Spanish is easier to learn than Finnish!
Anyway, I think Lakota, Cherokee, or Navajo are your best bets. Those are the ones with the most resources. Navajo is tonal, so that might put it out of the running. I do know that Cherokee is a lot easier to pronounce, however it does have a strongly agglutinative grammar. Lakota on the other hand doesn't seem to be too hard as far as grammar goes, but it's harder to pronounce.
Also, looking at numbers:
Cherokee: 15-22,000 speakers
Navajo: 178,000 speakers
Lakota: 8-9,000 speakers
Navajo is going to be easiest to find resources on now that I look at it. I might consider learning it myself!
Oh, wait. I just looked at your profile. You live in Oregon. Eh, I'm not sure which one would be better. I think they would all be equally hard to find resources on. Navajo is spoken in New Mexico, and somewhat in Arizona. Cherokee is spoken in Oklahoma and North Carolina (although I think the most productive dialect is the Oklahoman one), and Lakota is spoken in N./S. Dakota.