I've been tagging profiles who connect to gateway ancestors with the EuroAristo template for a while now, and after correcting a bunch I've seen the phrase 'middle class' in many profiles which is there for modern eyes but is very deceptive and causes some errors. You have to be extremely suspicious when you look at family histories that claim descent from nobility or royalty to evaluate their social class. While we can approximate it using wealth or status, there was no middle class in 17th century England.
Ask yourself "Was this ancestor a gentleman"? Property or a title makes this easy. One hint is occupation - military officers, clergy and lawyers were deemed gentlemen and would marry daughters of gentlemen. It was much more difficult to get into these occupations as a freeman, but certainly happened. The last two were usually achieved via attendance at University, which is not that different than today!
Many immigrants with wealth had some background in commerce which was definitely a lesser occupation for sons of gentlemen because this is where relatively wealthy freemen and poorer sons who had no inheritance mixed together. Its not a 'middle', it's two hierarchies which one could pop over into one or the other track based on your income and conduct. Along with University attendance, this is why I think people like my ancestor John Weston's children and grandchildren were able to join the gentry easily even though socially he doesn't seem to qualify.
Farmers and more mundane occupations (wheelwright, glassmaker) were definitely not considered gentle no matter how much $ you earned and it would be very unusual to marry daughters of gentlemen. Many early immigrants were farmers so I always wonder how the son of a lawyer comes to New England and starts farming. But these occupations were so important in colonial times they were very important people with high status akin to gentlemen in England.
Life in the colonies for freemen was in many ways much better than their life in England, but for gentry it was significantly more difficult so outside of the upheavals surrounding the English Civil war the odds of one of the upper class emigrating are extremely low. The economic circumstances made everyone very similar unlike in England, and the economic similarity grew into what we like to call 'middle class' today.