Aside from any poliical issues, both Puerto Rico and Guam have National Olympic Committees and are therefore formally invited to to participate in the Olympic games. It doesn't actually matter if they are classified as a "Commonwealth associated with the United States". As long as they have and hold formal IOC recognition they can send competitors.
Puerto Ricans are US citizens (with no US voting rights), but are instead self governing since 1952.
Puerto Rico has been participating in the Olympics since 1948 in London.
Puerto Rico even sent a very small delegation to the 1980 Olympics in Moscow despite US boycott.
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