You’ll be glad to know that we went back in time and took your advice many years ago. Not just some years even, every year! PyCon India is taking place in just a few weeks and PyCon Africa just a couple of weeks after that. Amazing, isn’t it.
As for the much more interesting question you’ve managed to not actually ask as far as I’ve seen: “Why is PyCon US (or PyCon NA because of the years it’s been in Canada) the only conference directly organized by the PSF when there are now so many?”. I can’t shed as much light on this as Thomas did in his excellent post above but I was (mostly) there for it so I’ll try. PyCon US started out as a fully volunteer-organized event, but the community was pretty small and it just so happened that the same people as doing PyCon US were also doing most of the logistics and planning for the PSF, not out of favoritism but because the few people interested in that kind of (fairly tedious and difficult) work were naturally interested in both topics. There was a similar event in Europe which started before PyCon US (just “PyCon” at the time), EuroPython’s first event was in 2002 and PyCon in DC started in 2003. EuroPython quickly set up its own management organization, the EuroPython Society, as I understand it largely because it was logistically difficult to channel EU-based donations to a US bank account and then back to EU vendors. These days the PSF has a lot more capabilities for such things but this was 20 years ago and it made more sense to keep them separate. And so for largely historical reasons, it has remained this way. As other regional PyCons have started, some operate under the auspices of the PSF, some use an existing regional FOSS non-profit, and some found their own organization as EuroPython did (with the legal and logistical help of the PSF team to make sure they do things in a way best for their local community).
As for the increasing professionalization of PyCon US, this was also kind of accidental, or at least unexpected by the PyCon US team. For those not involved in the process, PyCon US looks for new locations in two year blocks. A big part of selecting a conference site is a proposal written by the local community there. In ~2006 we were looking at available options for 2008, and part of the bid submitted by ChiPy, the Chicago Python user group, was that they had priced in help from a professional event planner team (CTE) to offset their worries about having less on-the-ground talent in that area from ChiPy itself. Their bid ended up being selected for a variety of reasons, and at the time we all pretty much said “well this CTE team seems nice, we don’t really think we’ll need it but they can help a bit". This was very much not PyCon US seeking out professionalization, it was suggested by the community team and accepted as an experiment. PyCon US 2008 was twice as big as 2007 and while we had some sharp growing pains that year (like 2025, 2008 was an incredibly hard year on non-profits as the world economy fell over and caught fire), the CTE team proved themselves to be extremely capable and helpful in navigating difficult problems. Despite the issues from 2008, the overall response from the Python community was they appreciated the larger and more polished event, giving room for more talks, more open spaces, and generally making the event more valuable for everyone. So we continued that trend, trying to fit in more of the things everyone wanted, and with that came more and more organizational duties. In time, the job being done by CTE was brought in-house to the PSF to help keep costs down and ensure we had full control over staffing. Our event planning crew eventually also started pitching in on general support and fundraising, which helped not just make PyCon US bigger, but gave the PSF resources to start supporting more community work elsewhere. And fast-forwarding a bit, we get where we are today, with PyCon US being the only event organized by the PSF team, not because of a sinister conspiracy, but just slow growth from volunteer roots to what we have now.
Hopefully that sheds some light on the organization structures of PyCon US over the last few decades.