It bugs me how much Valve will plop maps for their updates but not want to make their tools open-source or do anything to help the map-making community. Not saying that there's an entitlement to the tools but it would really make life easier for people who are putting a significant amount of time and have become a vital cog in their wheel of updates.
It kinda bugs me too, throwing some money our way is definitely a huge help but realistically, if you manage to feed yourself and have a roof, it'll be difficult to cover the costs of software licenses to get the job done, we're still kinda left on our own.
Being able to get shit done on your own is great tho. The thing I've realized about source over the years is that if there's a part of the workflow that you don't like, there's usually a lot you can do about it by building tools on top of what valve provides. The base toolset is primitive but the little we are given is very good and easy to build upon. We could have crazy tools and push source really far but it's difficult to justify building those tools when there's no money into it. So in the end what we're left with is a bunch of community tools that do the bare minimum and usually those tools aren't even maintained. It sucks but it is what it is.