Thanks for the recent post and new information about Thomas possibly being in Charlestown with Richard Perry. According to the court records of New Haven Colony when Thomas got into trouble, Perry had another servant too. (One who got into trouble repeatedly, apparently. And, I believe was at one time kicked out of the colony.)
 A COURT HOLDEN 4th OF DECEMBER 1639.
Thomas Manchester, servant to Mr. Perry being accused by his Mar for being druncke, and for giveing his Mar vncomely language for wch his Mar having given him some correction, the court (onely) caused him to be sett in the stocks for a certaine time. Nicholas Tanner, servant to the said Mr. Perry, for drunkennes and abuseing his Mar in wordes, was whipped.
So, if Thomas was in Charlestown earlier, he couldn't have been left with the land to work it if he was in trouble already in December of 1639.However, Mr. Perry may have had other servants/employees working for him of whom we have no record yet.
If Perry was a part-owner of the Hector, he and his family may not have been listed as a passenger. Most of the ships were owned by groups of men--even down to 1/16th in one case I saw.
To be 'admitted' to a community meant you had the status of a freeman, one who could serve and vote, as opposed to being a craftsman or servant.
There was a shortage of currency in those days and 'planters' were awarded land and encouraged to stay and establish the colony by becoming a contributing member. There was some competition for new arrivals, apparently, because Winthrop was eager to encourage more settlers to the Boston area, having wooed the Rodgers/Rowley group and the Davenport group. Davenport, at first encouraged the Rodgers/Rowley group to join in the settlement of New Haven.