We can extend it a bit more:

Can one sin and then repent?
Of course, some shout aloud.

Can one repent and then sin?
Nope, some would say emphatically.

Can one sin and repent and then sin again and repent again?
Hmm, sure!

Can one sin and repent and then sin again and repent again and then sin a third time and repent a third time?
Hmm, why not?

Can one sin and repent and then sin again and repent again and then sin a third time and repent a third time and ...... then sin 77th time and repent 77th time?
Hmm, tough case. But Jesus said we ought to forgive our brother 70 and 7 (or possibly 70 times 7) times. So I guess we have to forgive him as many times as he sin against us and God? I bet he has to repent that many times too to be acceptable before God.

So can one endlessly sin and repent again and again and ...... again?
Probably not, since apostle John teaches clearly the a child of God living in light shall not love darkness and will not continue in sinning.

So how many times is the "right" number of times for sinning and repentance?
Don't know for sure.

This perplexing puzzle lingers on in sinner's mind who is planning for the next round of sin and repentance.