Nice question.
I am now working in Ruby, PHP and ActionScript (the least dynamic of the three) instead of languages that I would prefer, like Java and C#. But beggars, I mean, workers in this economy, can't be choosers. Or rather, you have to choose your battles and your master.
It's hard to compare Ruby and Java because they've got more than one difference, and you only asked about the dynamic/static thing (and not even about the strongly vs. weakly-typed thing!). But on that front, what affects me most is always the IDE. I was always horrified when other Java programmers used Notepad or Textpad to write code, and nowadays there are just too many advantages of a good IDE for that madness. Not true with Ruby! I use Netbeans and it does really well, but one of the main differences is that I have to actually type code. Autocomplete, for me, was/is a way of life (I write SMS messages in full English/Spanish with the predictive dictionary, for instance, and never use abbreviations) and writing Ruby code does require more work.
So at first it was painful and I was constantly looking at, for instance, function names of classes that I had written (or that are part of Ruby) just to get the spelling right! So that sucked, I thought, and I continued to think that until...
I moved back to ActionScript the other day, and to get my IDE autocompleting (FlashDevelop or FlexBuilder) I declare all variables with types (strongly-typed by choice, if you will)... and suddenly I thought what a friggin' hassle!
And then today I had to do some feature additions on a Ruby project and it felt free and cool. The code is clean, and why would I be informing the IDE of what I'm trying to write anyway?
So I would say that 1) the biggest challenges are learning the language and the framework you're working in, like always 2) it's been amazingly fun and deeply eye-opening. New languages always carry new things with them, but dynamic languages just feel different. And that's just the kind of thing that gets you to wake up at 7am and do some coding on a Sunday morning before falling asleep again.
I like programming and like most of you, I've spent some time with stored procedures, XSL, static, dynamic, whatever... it's all fun, and they all feel totally different. In the end, the framework you are working in will be the thing that will convince you too stay or not (if you have a choice), I think, but languages are to learned, studied and experienced, not compared.