Question

by the year 1999, my friend Marcos ... how to play a lot of songs on his guitar.

Answer 1

Até o ano de 1999 , meu amigo Marcos tem como tocar um monte de músicas em sua guitarra .
 = By the year 1999 , my friend Mark is to play a lot of songs on his guitar .

Answer 2

By the year 2099, my friend Marcos will have learned how to play a lot of songs on his guitar