From your handle I'd guess you were a Southron like Jefferson, so your comment on Jefferson's financial problems and proclivities were somewhat surprising. I suppose if you're from a Puritan background it would seem strange. I think the most charitable thing that can be said here is the Jefferson's attitudes towards money were not atypical of his class and time. The British aristocracy, and the Virginia gentry in imitation, was typically land (and slave) rich, but cash poor. To conduct their lives at all, some sort of credit system of borrowing against future crops for both expenses and capital needs was almost essential. Jefferson's habits were expensive, but he was not, as were some of his peers, a compulsive gambler or rake-hell who spent his patrimony on fallen women. IIRC, when his father died, Jefferson inherited lands already heavily encumbered, and never worked his way out from under, indeed made it worse. As to his leaving his family, that, too, was not unusual in that period: men were often away (whether at sea or at war or for business) for years at a time. Jefferson could almost be considered a homebody by contemporary standards, except for the time he spent abroad or in Philadelphia and Washington in government service.
Jefferson's relations with women are not very clear. That he did not remarry is surprising, but, then, people took promises such as the one he made to Marth more seriously than we do today. Fascinating subject.