Dale
I'm not sure you have a context for the early arrivers to Massachusetts & that may be part of what's throwing you?
Over 20,000 people left (what is now) the United Kingdom between 1620-1640. Then it stopped because of Cromwell's Revolution. The religious troubled were over (for a while). In fact quite a few colonists returned .
The migrations were to
A) Virginia - "merchant / adventurers"
B) New England - "saints & sinners"
(Nb: of course I am speaking in broad generalities)
John of Dedham was a B.
So - who were these people, how did they get here, and why?
They took ships. They were recruited. They traveled in family groups. They looked for strong, craft skilled, working persons, willing to pioneer & take a chance. Many were religious refugees as mentioned until you're sick of hearing it.:):)
If John came about age 20 as a single person & he had some skills on offer - farming of course, but weaving, carpentry, etc were also recruited - he is an excellent candidate for pioneering.
That he stayed in Dedham (Justin & I both had ancestors who moved on) suggests he fit in comfortably. He had his allotment, he raised his children, he didn't get into trouble, he did some service to the town.
And then in the next generation his children expanded their farms, or started to move on to new territory opening up in Connecticut - as your ancestor Samuel did.
I don't want to use the word "typical" because to paraphrase Tolstoy, every family is unique. But certainly there is nothing that seems unusual from, say, my farming ancestors of Concord.