The "Fledgling" story arc isn't the best way to enter the series, IMO. Not because it isn't interesting - it is - but because the first book is basically a YA novel since its main character, Theo, is so young at that point. You watch her evolve but you don't truly understand why certain milestones have a much greater importance than they appear. I don't think you can really appreciate certain characters, like Prof. Kiladi, because you don't understand how they fit in the main story arc. You can't really appreciate how circumscribed her life is by the university culture because you don't yet know what her birthright is. You have no reason to wonder how her mother is going to fit into that birthright. There are layers to the story that you are missing simply because of your entry point into the series.
IMO, "Fledgling" is best read after "I Dare" in the Agent of Change story arc, because that's when Theo first appears in the main Liaden story line and when you really need to learn who she is and why she tracks down who she does.
The Theo Waitley stories and the Jela/Cantra (the Crystal books) make a great deal more sense, and are much more satisfying when they are used to fill in the details of people and events mentioned only in passing in the main story arc. Think of the Agent of Change story arc ("Agent of Change", "Conflict of Honors","Carpe Diem", "Plan B" and "I Dare") as the core play-by-play, and all the rest of the books as the color commentary. Another comparison would be to Eric Flint's "1632" universe where the main storyline involves Grantville and the area that is now Germany, while some of the subsequent books are focused on events happening in Italy or the countries bordering the North Sea. You can read the other books, but to really know what's going on you need to start with "1632" and "1633".
The scope of the Agent of Change story arc is much broader and gives a much better understanding of Liaden, Terran and Xtrang culture, which in turn provides many more "a-ha!" moments when the other books fill in the backstories of characters and events.
It's possible that by approaching the series from the "Fledgling" vector, the Agent of Change arc will provide those "a-ha" moments, but it's not the way I would recommend approaching the series. My preferred reading order (slightly out-of-date since it doesn't list the latest books) is
https://www.mobileread.com/forums/sho...44&postcount=2
Just understand that "Local Custom" and "Scout's Progress" are referred to as the Space Regencies for a reason. They detail the courtship of the two sets of parents of the main characters and the customs of Liad and the behaviors of Liadens. They are not, however, lovey-dovey sexfests; just more narrowly focused on the interpersonal relationships - more "opera", less "space", so to speak. Think a Georgette Heyer story set on other planets involved different social mores. They give you a better sense of who and where the later characters come from, and what events shaped them.
Count me as another person for whom this series is my absolute favorite science fiction series.