QUOTE: the part of the Windows market that they are chasing (the Windows desktop) I see as a model with a limited future as a mainstream model

I guess that depends on what you mean by "desktop". If you mean "end user usability", then it makes sense to try to address that niche. If you mean "mid-tower sitting on a desk", then I guess that's not as important -- but I'm not sure how addressing the needs of laptops (for instance) would specifically avoid the "mid-tower sitting on a desk" needs as well.

The problem, as I see it, is not that someone's trying to address the needs of someone sitting in front of a computer (such as a laptop or development workstation), but that someone's trying to do so by mimicking an OS that does it poorly.

QUOTE: Why not make an OS with a shell that is perfect for managing servers (yeah yeah, I know, it's called "bash")?

Oh, hell no. Bash is garbage. If you have to write shell scripts, write them in sh, for standardization and portability purposes if nothing else -- and if you need more than sh use a programming language for Pete's sake, not an interactive command shell syntax. If you have to have a feature-rich interactive shell, use something like mksh or zsh. Bash is too bloated, dependency-heavy, and perverse in its design to ever be mistaken for an elegant piece of software, and too short-changed, emasculated, and poorly conceived to fill the needs of someone who actually wants real interactive command shell convenience and flexibility.

I can only hope that "wink" smilie in your comment is meant to indicate facetiousness.

QUOTE: Microsoft's got a huge gap there, and with their constant investment in PowerShell it seems like they recognize it.

PowerShell is a platypus. Its designers seem to have been confused about what they were creating. It has some features obviously designed for interactive command shell use that make its suitability as a scripting language pretty suspect, and it has some features obviously designed for admin scripting and programming purposes that make its suitability as an interactive command shell syntax pretty suspect.

QUOTE: BSD gives me lots of reasons to stay... but if I want to break out of the Microsoft ecosystem (and I keep trying to!), I need a system that I get pick up and run with and not trip over the details.

Have you tried PC-BSD or GhostBSD? I think the latter is probably less mature, but I mention it because some people swear by it.

QUOTE: I keep slowly increasing my exposure to Ruby/Rails/Sinatra/Python/Django/etc. in an effort to find an open source, *Nix-y development experience that re-captures the joy of Perl while being modern and letting me fill the needs that I have.

Have you looked at Catalyst? It's an MVC web framework for Perl. I haven't used it, but if Perlishness is what makes it fun for you, Catalyst might be worth a shot.

QUOTE: erb18 does the same, though, which is "wrong", it should be calling /usr/local/bin/ruby18, to ensure that it always calls Ruby 1.8.

File a bug with the port maintainer. Check the ports pkg-descr file to see if the maintainer's email is in that, or check freshports online. You could file a bug via pr, too, but I suspect you would find it an aggravating experience.

QUOTE: And erb19 also always seems to call /usr/local/bin/ruby, which is "wrong" for the same reason.

Same deal as with my bug filing suggestion for erb18. In either case, if there's actually a problem there, it may get fixed pretty quickly.

I'd just change the default Ruby from 1.8 to 1.9 if it was me, though.