Looking to start traveling

Hello!

Im looking at starting traveling in the second half of the year. I will have over 2 years experience by the time I start, and have gotten a couple recruiter contacts. A couple questions I have as I start looking more seriously.

How does insurance/401k work? Would I need to stick with a single travel company to get these benefits? Am I able to switch between companies with contracts and have benefits for the period of my contract?

How exactly does housing stipend work? I rent a room from a friend. I have paid rent and the address is my permanent address but my name is not on utilities or formal lease agreements. Would I still be able to get the housing stipends? Do I need to create a more formal lease to qualify?

Any additional "I wish I knew this before I started" tips you would like to share.

Thanks!