Over the past few years, the Perl Foundation received a bunch of nice big donations to be used for Perl 5. Some of this money has been used to pay for work by Dave Mitchell and Nicholas Clark to work on difficult problems in the Perl 5 core. This has, in my opinion, been money well spent. Dave and Nick know the Perl core very well, and they've worked seemingly tirelessly to make progress where progress is not easy, and to fix things that nobody else wanted to touch.
There are problems with this kind of spending, though. One of them is that Dave and Nick are human resources, and not permanent assets. We can keep spending money on them for as long as they let us, and it will almost certainly keep being a good investment, but it can't go on forever. Another problem is that the rate at which we can fund Nick and Dave is limited, and we're not going to burn through all the money any time soon doing that.
Do we want to be in a rush to spend all that money? Well, maybe not a big rush, and maybe not all of it, but I think it sends a bad sign to donators when we don't spend the money we're given. Specifically, it sends the sign that we don't have any need for money, because we're not even really using what we have.
Then again, maybe we don't. Maybe the only things we should be spending money on are the YAPCs, legal issues, and some service hosting. There's an argument to be made for that, too. It's been said that when TPF spends money on some coding, it indicates that there are multiple strata of people in the Perl community: those whose work is blessed by "the powers that be" and those whose work isn't. Does this create a real disincentive for "outsiders" to contribute?
It's a big complicated question, all of which boils down to something like, "What ought TPF to do?" Maybe the answer is, "just what it's doing now." If that's the case, though, I want to feel convinced of it. Right now, I'm not.
I think I'm going to write down a bunch of ideas for how TPF could spend money other than conferences and paying for Dave and Nick. Implicit or explicit in these ideas will be my internal list of problems that seem worth solving but without obvious solutions that can be carried out with just some free time and good intentions.