Janeway Question ABout Her Ancestress

In this one episode, Captain Catherine Janeway was reminiscing about her 15x great-grandmother and said she had helped build The Millennium Gateway in 2000, which was a shopping mall. Then it goes into the past and shows this ancestor coming to the town where the GAteway is to be built, but she meets up with a bookstore owner (who looks like that actor that used to play the ecologist in the woods in the sit com about the Bigfoot, HARRY, It was called). First of all he was older than the ancestor, wasn’t he? Yet they became romantically involved.
The bookstore owner won’t sell his property to the big company that is to build this huge structure, and the ancestress helps him for awhile but then decides to move on. Besides, the big corporate guy has offered her a job in another town at her engineering work that would be good for her career, as she is an engineer. As she drives off in a snowstorm she says she has to decide soon whether she will go to this other job or go to Florida where she was headed in the first place, but she winds up going back to her new "boy"friend instead and tryhing to convince him to change his mind. She says what about the future and he says what about the past this is our home, etc. in this nice town like Mayberry. But she changes his mind when she indicates she loves him and he loves her and they go out and announce that he has agreed to sell so the big project of the Millennium Mall can happen after all. The people are rejoicing in the streets. Then the boss of the project says to this ancestress that she can have a job with the company anyways even though she hadn’t lived up to her parth of the bargain. But actually she did live up to it, she did persuade him, And anyway she is happy that she will get to be an engineer. However, they then go 15 generations into their future and Captain Janeway is shown as disappointed that after all her ancestoress was not the one who did so much to build this project as the family ancestry tradition had said she did. She is going to thow the picture of them away that somebody downloaded from the Ferengi data base but the crew point out that after all at least the family story was a tradition THAT INSPIRED HER AND MADE HER GO ON IN HER EDUCATION AT STARBOARD ACADEMY AND UP TO BECOMING THE CAPTAIN OF A WHOLE FEDERATION STARSHIP. I thought this was a good point, but the whole thing didn’t make sense to me since actually the ancestor did then work as an engineer on the project, so what is her descendant depressed about?