How does an American get a job in Puerto Rico?

Apply for one like everyone else.

How's your Spanish?

You apply for a job. Puerto Rico is part of the US, you don't need anything special.

There are cigar rolling schools in both Texas and Cuba you might attend.  To learn the basics of cigar rolling takes at least a year.  To become a master  'Torcedor'  will take many.

What they said but you'll need fluent Spanish, too.

You do know that Puerto Ricans are Americans, too? PR is an American territory. You don't need a passport to visit PR, and you don't need a visa to live and work there.

I think you might want to visit to get a sense of whether you really do want to live there, and while there, you can explore job opportunities.