Greetings,
Hell, I spend most of my time in Java, and I find the objc verbosity to be...uhhh...pretty familiar. ;)

Joking aside, I'll often take common ObjC patterns and 're-do' them the Ruby way so they're more efficient to the way my brain works.

As an example from a recent bit of code, you have:

      NSArray *dropTypes = [NSArray arrayWithObjects:"BookmarkDictionaryListPboardType", "MozURLType",
                               NSFilenamesPboardType, NSURLPboardType, NSStringPboardType, nil];

versus
      dropTypes = ["BookmarkDictionaryListPboardType", "MozURLType", NSFilenamesPboardType, NSURLPboardType, NSStringPboardType]

The first is remarkably flexible in rare cases, but exceptionally annoying for the common case.

To try and answer the questions, though...
  • What are the advantages of MacRuby over Objective-C?
    • An easy to learn, concise syntax in a language designed for the pleasure of programming but with enough power for all but the toughest problems
    • Being interpreted means you can try things very quickly, and not have to go through a compile cycle for each time you just want to see how something works.
    • A ton of 'gem' libraries that do very cool things in natural way
  • What are the advantage of O-C over Ruby?
    • Compiled, so marginally faster (although MacRuby's compilation is getting better)
    • All the examples of doing MacOS X programming out there are in Objective C, so you have to translate
    • A decent number of native libraries which, while you can use them in MacRuby, are easier to use in Objective C
    • iOS programming
  • Is Xcode's support for O-C significantly better than it's handling of Ruby?  Do I care?
    • Yes, it is better.  No, I don't find it better enough that I care very much.  Symbol completion doesn't work great in MacRuby, but it doesn't bother me much.
  • At this point I'm primarily interested in OS X development, but iOS clearly needs to run a close second.  What's the current status of Ruby development for iOS and is it likely to go anywhere in the nearish future?
    • The garbage-collection requirement makes this a non-starter right now.  It might get better, it might not.  I do iOS programming in Objective C, and Mac OS X programming in MacRuby.  It helps me keep my hand in Objective C development, so I'm always able to translate between Objective C and MacRuby, while letting me build a desktop app in my favorite language of all time, so far. :)
  • Any thoughts on the longer-term prospects of either language?
    • Ruby itself is likely to remain a strong contender for many years.  MacRuby has just started being shipped, albiet as a private framework, by Apple.  This bodes well, but as the Java OS X developers can tell you with a touch of sadness...things change.
Hope that helps some!

--  Morgan