It's fine to make estimates based on everything you know about him -- often for this period, some of the dates are simply unknown, and CT church records in particular were often lost or destroyed. See the discussion here:
https://www.wikitree.com/wiki/Template:Estimated_Date
Early New England rules of thumb:
I generally estimate based on knowing that first marriages in New England at this time happened around age 23; first births at 25; and if I'm looking at just one child, with no idea of where in the birth order, I estimate that the parents were about 35.
IME, for first marriages, the spouses are usually about the same age -- about 23. For marriages in mid-to-late child bearing years (widows and widowers) the women are younger than the husband, and still of child-bearing age; for late-in-life marriages, post children, spouses are usually closer in age again.
Use the Estimated Date research box -- for instance:
{{Estimated Date|Birth and Death}}
See this profile to see how that looks: https://www.wikitree.com/wiki/Church-166
More on estimated dates:
https://www.wikitree.com/wiki/Help:Estimated_Dates
To do further research on Jesse, Familysearch.org is free. Be aware that the research and sources vary from truly terrible to awesome and unique; check everything carefully. If you're looking at profiles in the familysearch family trees, some of the sources may link to paid sites. If something looks tantalizing, come on G2G and ask for a look-up; people are very generous. IMO, it's one of the pleasures of having a subscription.