It's a few things. One of the simplest reasons is as you identified, it's easier to get smaller donations from multiple people than it is to get one large dona

It's a few things. One of the simplest reasons is as you identified, it's easier to get smaller donations from multiple people than it is to get one large donation from a single company (although we do have large donations too ranging from 30,000/month and going downwards from there-- for all the PSF infra not just PyPI). Another part of that is a lot of this has grown organically over time and we sought out donations from different providers based on our need at the time. In addition, I can't think of a single company that actually provides everything we need except for maybe Amazon/AWS. On top of all of that the more we centralize our donations onto a single company, the more important a single company becomes to PyPI and the larger the amount of Risk we take on is. It would be a lot harder to find a replacement for all of the things we need all at once than it would be to find a replacement for just a single service. All in all, managing these accounts is not particularly hard (though in some part that's likely because the set of people who has access to any of one of these is pretty static). Most of them provide some sort of standardize API access that doesn't really change based on who is providing said thing (in general, we attempt to rely as much as possible on "Hosted X" where X is some OSS thing we could possibly run ourselves or switch to someone else's "Hosted X" if need be. It's not mandatory but the harder it would be to switch the more we factor that into our decision (for instance, our use of S3 is pretty simple so we don't worry about their proprietary API because it wouldn't be difficult to modify the code to do it differently).