Are the aforementioned prayers considered valid (shortened and combined) with repeated travel for the same distance and duration? Is this consistent act considered travel that permits shortening and combining prayers? What is the ruling on combining the Asr prayer after the Jumu'ah prayer?

If your journey from your city to your workplace city permits shortening prayers (a distance of approximately 80 km), and your stay in the city of work does not reach four days, then it is legislated for you to shorten prayers, and it is permissible for you to combine prayers, either by advancing them or delaying them. The repetition of travel or traveling by car does not affect this. However, if the conditions are not met, then it is not permissible for you to avail yourself of the concessions of travel. It is permissible to combine Jumu'ah (Friday prayer) and Asr prayer in the rain, and this is the most preponderant opinion, although leaving it as a precaution is better.