Not sure if this question is specific enough to qualify, but here goes nothing:
So, Spain's first American colonies right after Columbus's "discovery" were in the Caribbean, right in the Taino homeland. Before they acquired the rest of what is now Central and South America, they spent 2-3 decades interacting with the Taino. But, when the Aztecs and Incas were conquered, many priests soon learned and published books in their languages. I know those two peoples had larger and more populous empires, but the Spanish still spent a while with the Tainos, which would make sense to learn a bit of the language.
As far as I know, there are no books dealing with the Taino from that period. I know some words and basic grammar were recorded, but not enough that an entire textbook or chronicle was published.
Well, the Taino werent crucial for the administration of New Spain, and viceversa had little legal claims to their own land, sadly the Tainos as a people died relatively quickly after the arrival of the spaniards, the same didnt happen in the former Aztec and Inca empires.
Both had on one side, huge populations and had turned their languages into a kind lingua franca in their respective regions, and on the other hand, in many cases mantained direct rule over their territories for a century or so after the conquest, many of the authors of that time (Chimalpain or Tezozomoc) wrote not with the porpouse of recording history (though we are very thankfull they did), but with the porpouse of establishing legal ownership of their own lands, for a time the spaniards recognized these claims until around 1585, when their hold in the regions was more firm and they could start taking direct control over America.
Even then, the take over was never full, spanish was only spoken by around 42% of the population at the time of the Mexican independence for example, and many of those were as a second language, not as their mother tounge.