One thing that intrigues me to this day is the so-called "Lost Colony" of Roanoke, which actually the first English settlement to be established (even earlier than both Jamestown and Plymouth). However, due to bad luck, poor planning, hostilities with the Spanish and of course the mysterious disappearance of the colonists (leaving behind just the carved words "Croatoan"), the colony pretty much failed.
Therefore, my question is how can the Roanoke Colony evade this fate and meet the same level of success that Jamestown was able to achieve? And what are the implications further down the road for the English/British colonies in the New World and beyond?
The Croatoan "mystery" was actually solved 30 years later, some 400 years ago, in spite of the fact that many believe it was unsolved. Under pressure from the hostile tribe nearby, the settlers abandoned their colony and went into hiding with local tribes who were more friendly. From there, some died, others were captured when (years down the line) the friendly tribes were conquered by other hostile tribes, and yet more integrated with the natives and lost their identity. There are some quaint stories of Indian tribes a couple of generations later who had the ability to build two-story huts in their villages, as well as blond-haired, blue-eyed natives being found a century later or more and even one story (I'm not sure if it's true) that something like 120 years later or something crazy, some English colonists were amazed to make contact with a tribe of natives who had never met Europeans before...and yet they spoke a dialect of English fluently. May be nonsense, but it's an interesting story.
As for what would happen, it's hard to say. So much of it depends on decisions made and how things like contact with natives would go during the period when they were still unable to dominate the natives. Even setting survival or even flourishing of the colony as a minimum requirement doesn't define whether they will end up making lots of enemies and being penned in and fighting their way to survival, or being universally popular and spreading out through diplomacy.
One interesting thing about the Roanoke colony is that the original intention was to have all the natives they found perform a ceremony of feudal homage to Queen Elizabeth, through the person of the Governor of the colony. They largely failed to do so OTL - most of the native tribes were insulted to be asked to perform a European ceremony, others declared that they had no need for a coronation ceremony, and the one time they actually managed to perform the ceremony, they had to capture the chieftain to force him to submit, even going so far as to man-handle a crown onto his head, in the most bizarre act of involuntary rank elevation I've ever heard of. Anyway, the intention was to turn America into a feudal state, with land being bought for settler cities to be ruled over by English nobles, and the natives populating the land in between in the style of manorial villages with their own liege lords. I'm not sure how this could be made to work, since it was so unusual and unwanted for the locals, but if it were to work, it would produce a radically different social composition for the colony - at least, unless somewhere down the line some Governor or other decided that he was frustrated with the natives and decided to kill them or drive them west, thus probably eliminating the bulk of the differences between TTL and OTL.
