I ended up solving the calendar problem for free -- and I'm very happy with the result. In iCal, you can create a Google account that will cause the Apple calendar to sync with Google (and thus with your Droid) every 15 minutes. You can also force an immediate sync anytime you want to. Here's the Google help page that tells you how to do it:
Get Started with CalDAV - Google Calendar Help
As for using the Droid for business, I've had only one complaint so far, and it's minor: It's nearly impossible to sync my Apple Address Book with the Droid. For some reason, they made the calendar easy to sync and the contacts hard.
But this is minor. For one thing, I'm told that Snow Leopard (the latest Apple OS) offers an automatic sync between Address Book and Google Contacts, and I plan to upgrade eventually. So that will be solved. As an alternative, I could use Busysync or The Missing Sync to keep the Droid contacts current. Friends have particularly recommended Missing Sync, which you can read about here:
Keep your life in sync with The Missing Sync for Android from Mark/Space
But pending my upgrade to Snow Leopard, I've just been updating my contacts manually on the phone -- a pain, but not permanent.
All in all, I'm really glad I got the Droid. I've found it very hard to get used to -- a good deal more complicated than the BlackBerry -- but once I figure things out, I find the features work well and the phone is more comfortable to use (plus cooler) than the BB.
Hope this helps. Bear with the Droid -- the getting-acquainted phase is rough, but you'll come to like it.