For a long while, there were also no debuggers for 1.9.1, which is a big deal for some people. Mark Moseley has done a lot of work to get them working on 1.9.1 so luckily this isn't really a concern any more.
http://github.com/mark-moseley
I made Ruby 1.9 my default Ruby using Macports (using the +nosuffix variant) a few months ago. Other than finding a few trivial bugs in my code and some other people's, it's been painless; though of course your mileage may vary.
It's finally time to start developing entirely in Ruby 1.9 guys. Trust me.
Our 1.9 deployment is Nginx -> HaProxy -> Thin
I had trouble getting Mongrel to work in 1.9 (it was my favorite in 1.8) although apparently you can do it. Thin just worked(tm) so I switched to it painlessly.
Monit may be harder to set up, but it works very well once it's running.
Ruby has a memory issue with long running processes. They seem to grow and grow and need to be restarted when they get out of hand. People commonly use Monit or God for this.
When you use Passenger, you can have it restart your processes after a certain amount of requests to prevent the memory leak issue, but when it happens it seems to block all requests to all processes for a short time, which is annoying to end users. It means your site can be speedy and zip along, then just pause.
Of course I blew everything away upgrading to Snow Leopard so I'll have to replace/upgrade with 1.9 again (though I'm also considering Ruby Version Manager).
Also, running on a Mac, it is easier to use whatever Mac is using so that your code has less bugs across different dev machines.
Afaik 1.9 didn't address this.
im soo much more productive when i can set a break point and see why my flow isn't working.