Wasn’t Roanoke the first colony that failed? And it was because they generally didn’t have enough supplies? I would take more food and people since Jamestown later fails because no one was growing food and people = stability. Tools to do farm work would be good too. I hope my answer helps you a little bit, however I would add more to it. (I don’t know what type of answer you need so I left it kinda vague, sorry)
