I've been considering this topic over the last few days.

Though I can’t be entirely sure, Norland Park seems to have passed down the generations without an entail for at least some of the time. The old Gentleman evidently inherited it without one. This is obviously a personal opinion, but it appears to me he was planning to just pass the estate along to Henry as he himself had received it, that is bequeath it to him with no strings attached. Then when the John Dashwoods showed up for visits with Harry, the little boy influenced him to reconsider a more traditional path. It may not have been so much his cuteness factor, etc. but I feel the toddler triggered thoughts of future generations with the following possible reasonings attending his decision: (1) I like your summary of how the uncle might have observed Henry’s management skills with money and might justifiably have been wary. (Although ironically, when you think about it, estates were passed on to eldest sons, regardless of their potential with money. Witness Tom Bertram.) Nevertheless, the uncle had the liberty to bypass any doubts he might have had about Henry and ensure the estate remained in the male line. (2) Accompanied by his observation of Henry’s managerial skills with money was his nephew’s financial distress in being able to provide for the female members of his family if he passed on before he (Henry) could accumulate enough money for their care, which likely led to the conclusion of the possibility that the estate, could in the future, be parceled out among the Dashwood sisters ending generations of a legacy. (3) While Norland would not be moving in a direct line among the male members, it would still be male oriented and remain in the family.

>settling an estate in consideration of one's fondness for a bunch of young female teenage relatives would be unheard of.

Quite true: my Norton Critical text footnotes the following as concerns the heritage line “...---but to a child of four years old, it was secured, in such a way, as to leave to himself no power of providing for those who were most dear to him, and who most needed a provision, by any charge on the estate, or by any sale of its valuable woods.” The footnote states that “R.W. Chapman suggests that Austen emended to charge (a payment from the estate) because her brother advised her that no sensible man would consider dividing the estate to begin with.” I believe this confirms your point and I’m aware that this would appear to contradict some of what I said above but I’m coming to that. :)

Henry’s son John must have visited him at Norland before he was married and likely after he married Fanny before they had Harry and it doesn’t appear the old Gentleman ever had any thoughts of necessarily entailing the property to go to John. It’s when little Harry shows up that he seems to have been prompted to think about the entail. Here’s my take on it: I don’t feel that the uncle actually thought much about the inheritance in a concrete way at the beginning. In his mind his nephew was next in line and it would go to him. When they moved in with him I feel he was easily distracted by his sensibilities of fondness and gratefulness for their care, concern, company and affection and continued to just let things drift. The girls were initially quite young too and no doubt were little-girl cute, Margaret, probably, quite the cute and charming toddler herself, certainly not too much older than a toddler. Years later, when the charming Harry, a male, appeared on the scene the uncle’s senses kicked in gear and he realized he wanted the continuity of the estate to proceed in the male line and wrote/renewed his will to reflect those wishes. I’m not sure of the soundness of this and I know it veers a bit from your ideas on the subject, but I’d be interested in your thoughts of this version and anyone else please feel free to chime in. Now, here’s what I’m wondering (rhetorically really): I’d be curious to know what the uncle would have done if the John Dashwoods had never had children or if Harry had been a Harriet.

Finally, your statement about his fondness for a bunch of teenage girls not having a chance of superseding his decision in relation to inheritance brings out another truth that’s been stated in this thread: girls did not count for much in relation to boys. [Little Harry’s attractions outweighed] all the value of the attention which, for years, he had received from his niece and her daughters. Quite sad really, how the smiles, baby talk and noise of a little boy could outdo the years of affection of the girls and their mother. I read somewhere that the next sentence was meant to be sardonic, He meant not to be unkind however, and as a mark of his affection for the three girls, he left them a thousand pounds a-piece. When I look at it this way I realize that while he was not so thoughtless as to leave them nothing, it makes it easy to see that essentially an 'unkindness' was rendered. I suppose his society would not have censured him but it would not have precluded him from doing more to repay their kindness by ensuring a reasonably decent survival for the girls.