I came from a heavy Java background, with lighter amounts of C++ and also some Lisp/Scheme as you have - I've been doing iPhone application development full time since the SDK release. Here are some thoughts I have on the questions you raised.
What one would need to learn?
You need to learn Objective-C, the language - a helpful guide showing you comparatively how things are done in C++ (and some Java) compared to Objective-C is:
http://ktd.club.fr/programmation/fichiers/cpp-objc-en.pdf
I found that very handy in quickly understanding the Objective-C syntax, since it's not a large divergence from C syntactically but is more so conceptually.
Beyond that, just like Java Apple's Objective-C has a very large set of foundation classes you can work with - just as rich in terms on string handling, internationalization, complex time/date support, etc. Just like Java, that will take some time to get used to - but knowing the Java libraries, a number of things are conceptually similar. The GUI classes are also extensive and pretty powerful, as are some of the other frameworks like CoreData and CoreAnimation. Happily I find the documentation very good, it's well integrated with XCode and even has sample code links in the docs.
Also, the GUI development tool Interface Builder is very good to work with. I never found GUI builder tools of much use in the Java world (or really in any other world) but the model that Objective-C uses where you basically are creating objects that get wired up at runtime to your code, works really well and does enhance productivity. It's good to know how to do some things manually to understand what is build built by the components you are adding, but I'd start learning how to use Interface Builder when possible, early on.
I also highly recommend the O'Reilly safari online book service, because you can hunt down a few books that are of use and search for extended examples on something you are having trouble with for a marginal monthly fee. You can get the widely read Hillegass book there, among others.
How long would a good developer need to get up to speed?
That's tricky to say, because it depends on just what kind of app you are trying to build. Some areas of the frameworks and GUI components are easier to understand than others. But, I would say probably a month or two of full-time working with it would yield a pretty decent level of familiarity, and you would be productive before then. Someone with a good background in a variety of languages will have an easier time I think. Also it pays to really learn the ins and outs of XCode, because it's a very powerful tool but at first may not seem that way depending on what IDE's you are used to.
One thought is that you may way to go to a training session somewhere. There's actually an in-depth iPhone conference in Denver just a week from this post date, 360iDev:
http://www.360idev.com/
(Disclaimer, I am a speaker at a few of the session there)
Although if you do not yet even have a Mac, It may be a little too soon for that to be of full use. You could check around for other such conferences, or other places that offer training.
Are there any non-obvious expenses that might arise from pursuing this route?
Financially? Not really. You can use pretty much any modern Intel Mac to develop with and it will work great, with the caveat you should have 2GB of RAM.
You'll need a device, but if you are not using features found on the phone a Touch is fine to develop against for all platforms so you could avoid a recurring fee if you do not need one.
Time-wise, as noted there are a large set of foundation classes and so that takes some getting used to. But one good thing about the mac as a platform is that while it differs from windows, it has a good Terminal app so you can be productive in a standard UNIX shell with all the UNIX tools you are used to having. You can even do command line builds although realistically you end up working pretty much all the time in XCode (though I admit to breaking out to Emacs on occasion when I need to do some tricky bit of editing better suited to Emacs' abilities).