When did ships REALLY arrive? Virginia Magazine of History & Biography, v88, pp 401-414, "Early Passengers to Virginia" (Avery E Kolb), clarifies discrepancies. Dainty (otherwise unmentioned) arrived in 1610. Swan and others arrived 1611, not 1610. Diana arrived 1619, not 1618. (Actually, in Mar 1618/19)
Is father of Thomas Jordan (jr) identified correctly, as Thomas (sr)? It occurs to me, that since C&P (in general) offers only abstracts, we might find more answers in the original Virginia Land Books. For example, in C&P v2 p358, the abstract for Samuel Jordan states only: "Samuel Jourdan, Gent, an Ancient Planter, 450 acs, Chas City Co, 10 Dec 1620, (Patent Book #8), p 125."
The complete record (one of the few presented in C&P) states that he was in Virginia for 10 years, names his wife, ... Perhaps the complete record for Thomas Jordan contains similar information? If, for example, Thomas had lived in Virginia for 16 years, when he was granted land in 1635, then we could infer that he had arrived in 1619, and was indeed the same person, as Thomas Jordan of Pasbehegh.
Also, the fact that Thomas (sr) died (1637) so soon after Thomas (jr) was born (1634), agrees with the small size of his family - just Thomas (jr) and Margaret are known. (No other aunts or uncles appeared at any of the weddings of the sons of Thomas (jr).)
Assuming we have properly identified the father of Thomas (jr), then we know that Thomas (sr) married SOMEBODY between 1625 (when he is single) and ~1633 (his son was born 1634). Perhaps a single lady, who was already in Virginia, in 1625? More likely, perhaps, someone who arrived later.