The reason you don't have to worry about dependencies with Windows programs is because they include _everything_ with them. You know how when you uninstall a program, it says "I think this isn't used anymore, can't be sure" for some files? That's because Windows has no concept of dependency. It uses a counter to figure out which files are being used. It's a crap system which leads to many, many problems.
RPM is a much more elegant system, and relies on dynamic dependencies to figure out _exactly_ what you need. You will not get "I don't think you need this, not sure" in an RPM-based system. However, since not everything is included, you've got to go to rpmfind and download RPMs, or use apt-rpm and download them from FreshRPMs. The fact of the matter is, you trade one set of problems for another. I much prefer RedHat's to Windows'.
gcc 2.96 isn't as broken as people make it out to be. 90% of the problems with it are people writing bad code that they expected would work with 2.95, and got screwed when a bugfix version hit.
I'll be honest - most Linux distributions assume you have network access. If you don't, then it should come as no surprise things don't work well for you. Personally, I almost never update major packages unless I'm moving to a new release of RedHat. OK, sure, I'll throw in a new version of Gaim or something, but that's hardly a major packaage. Python is massively important - RedHat's tools are primarily python based.
You're really between a rock and a hard place if you have no net connection at home. There are some distributions that might be more to your liking, such as Debian or Gentoo, since you can keep them on the cutting edge, but unfortunately, these all depend heavily on internet access.
I am somewhat surprised that you find RH 8 to be buggy. It's certainly not perfect, but I've found it remarkably stable and fast. I'm using it on my laptop right now, in fact, and that's just a lowly P166MMX with 96mb of RAM. Maybe try RH9?