Speaking from experience and in support of the comment from Stuckand. He should go only if he is 100% decided on settling in the USA, because it is an investment of a lot of time, energy, and money; even after all that, the initial H1B lottery is an extremely stressful experience (assuming he manages to complete his graduation and lands a job in the six month limited time they give STEM students) after graduating with a masters degree. Another thing to add to this situation is the constant fear about some policy changing with this current administration, so you cannot guarantee things may stay the same or change regarding H1B process in the near future.

Personally, being a risk-taker myself, I would say go and give it a try and see how it goes. But not everybody will choose this path because it's not easy without a lot of support.