In my job, more and more I find that we end up building distributed architectures, i.e. multi-server installations where services are routinely spread around 20+ Windows boxes, plus the occasional Unix. These services have specific startup and shutdown sequences and dependencies, so they can't just be set to Automatic startup; we usually provide batch files to manage them, but this is quickly becoming ugly and unreliable as the number of machines go up every year. It's also tricky to test actual service availability -- some are binary-based, some are HTTP based, some are Weblogic services, etc etc etc... So I'm investigating alternatives.
The first, natural choice for me was obviously Python: it does everything I need, it's flexible etc. However, distributing scripts to customers is a bitch; either you compile everything with cx_freeze (crashy) or py2exe (no python 3! no 64bit bundling! party like it was 2004! have fun tracking down which un-redistributable DLL or manifest you need on each release...), or you drop an entire environment and teach the customer what python is -- not ideal.
The traditional "native" approach to these problems in the Windows world is VBScript. It's fairly flexible, doesn't need to be deployed on Windows Win2003+ (yes, we still deal with loads of Win2003 servers), documentation is extensive and there are plenty of resources out there.
The problem with VBScript, apart from the ugly syntax and pseudo-OOP quirkiness, is that it's clearly seen as legacy by Microsoft. Year after year, running scripts becomes more cumbersome, security checks increase and new technologies don't expose the necessary interfaces. Does it make sense, in 2011, to invest time and effort building solutions that are, de-facto, already obsolete?
So we come to PowerShell, Microsoft's "future of scripting", which must be the less intuitive shell I've ever had the pleasure to deal with. I simply can't get my head around the way it deals with input and output; it doesn't seem to have reference assignment, so you have to retrieve an object on every line before you can use it; the syntax seems to combine the worst of Perl and Bash, and it quickly becomes unreadable. Also, deploying it on anything older than Vista has to be done manually and has to be justified to customers.
I honestly can't see a good solution here. I keep looking at IronPython, but its infrastructure baffles me and I wouldn't know where to start redistributing programs (I don't use Visual Studio). It's clearly a second-class citizen in the .Net world, with all that it entails.
Maybe Jython? After all, the products we install will drop JREs absolutely everywhere, so I could leverage that. I'd like to avoid going full-Java if I can, I hate the whole byzantine toolchain and I'm not really up to speed with post-1.4 changes; plus, there's always a degree of customization required in each environment, so I'd like to keep stuff as easily-editable as possible.
Please feel free to drop any suggestions in comments, I could really do with them!