Apt-cyg, A command-line software installer for Cygwin
code.google.com
code.google.com
But my boss at my current job showed me a trick that makes it all better: run setup.exe, click the root checkbox, wait a few minutes for the GUI to start responding again, and install everything.
It's only a few thousand crummy packages, none of which conflict with one another, only totaling up to a few gigs. It takes all the hassle out of the process, you never get frustrated that you're missing some package's goddamn headers -- If you don't have it, it wasn't there, so you can go straight to upstream without worrying you're doing it wrong.
Instead, I first install the key stuff (wget, bash, whatever), making sure it is saved to disk, and then go back and gradually add pretty much everything.
Package management is a great idea. It's a shame so few OSs have anything like it.
I share your pain. My company makes me use Windows. Cygwin made it bearable.
It drives me nuts, cause I can't use a lot of these apps from CMD.EXE, FAR.EXE, etc. I guess I'll end up with "gcc" "gcc.exe" "gcc-SomeVer.exe" all pointing to the same NTFS file.
For programs that use the de-facto standard GNU Autocrap build system you can specify this by passing "--prefix=/usr/local" to the "./configure" script. It's also good to not install everything system-wide, and instead have a $HOME/bins prefix, with $HOME/bins/bin added to PATH. (And $HOME/bins/lib to LD_LIBRARY_PATH, and that pkg-config thing if it matters, etc)
But why did you call it "GNU Autocrap build system"?
It won't even make a /bin/bash -- unless you fuck shit up, everything outside of /usr/local /home and /root came directly from the FreeBSD project, period. You can checkout the source to your system's entire userland from one repository, and build it with one make.
I wish there was a nice Linux distro that held itself to this. Gentoo makes a nice distinction in portage between the necessary system packages that come built in the tarball and the world packages that you installed and care about, but it mixes them together in the filesystem.
There is no such thing. A 1.5TB disk is around $100.