Apple has long had trouble balancing its iCloud sync service with manual iTunes syncing, to no one's surprise. Sync is hard, and when you offer users multiple ways to put data on their devices, something's bound to get borked in the process. iCloud Photo Library is no exception—the service isn't on the Mac yet, which means that if you want to use it on your iOS devices, it'll effectively wall off your iPhoto library from your mobile lifestyle. But we've got a few tricks to get those iPhoto images back onto your iPhone or iPad.
iCloud photo limbo
Normally, when you sync data via iCloud and connect your device to iTunes, Apple walls off manual syncing for iCloud-synced items so as to avoid confusion and duplicates. Both your computer and iOS device should be on the same iCloud account, after all; everything should be synced over the air, with no need for manual tethering.
With your contacts, calendars, and music (presuming you have iTunes Match), this is true: If you plug in your device and open iTunes to one of those tabs, you'll be greeted with text noting that your data is being synced over the air via iCloud.
But Apple's new iCloud Photo Library option is in a special limbo: It's currently only available in beta form to iOS devices running iOS 8.1 or higher, with no support coming for the Mac until early 2015. (Sure, you can view images on iCloud.com, but there's no way to upload pictures to the service from your web browser.)
This means that if you want to enable iCloud Photo Library on your iOS devices, you'll be able to save and store all the images you've taken on your iPhone or iPad—but you'll no longer be able to sync images from iPhoto. Open iTunes, and the tab reads "[iPhone name] can access photos in iCloud. Photos can be downloaded to your device via Wi-Fi or cellular network."
Additionally, there's no way to trick your iPhone into having both iPhoto-synced images and the iCloud Library—if you disable iCloud, sync with iPhoto, and then try to reenable iCloud Photo Library, you'll get the following message: "Photos Synced from iTunes will be Removed."
As such, until next year, it looks like you'll have to choose which image library you want synced: your iCloud photos, made up of pictures from iOS devices, or your iPhoto library.
If you really want to get your iPhoto images onto your device (or into iCloud Photo Library), however, there are a few hacks you can employ.
Option one: Use iCloud Photo Sharing
iPhoto may not support iCloud Photo Library, but the app does support some of iCloud's older image-sharing features, including iCloud Photo Streams. It's also my first (and favorite) hack for getting images from iPhoto onto your iOS devices. Just select the pictures you want, then create a new iCloud Photo Stream from them by clicking Add To > iCloud or Share > iCloud.
Name your stream something like "iPhoto Images" and share it with your own Apple ID; within minutes, it should start to populate on your iOS devices under the Shared tab in the Photos app.
From there, you can view the images if you have an Internet connection, and you can download them locally to your device (which will then put them in the queue to be uploaded to your iCloud Photo Library) by selecting one, tapping the Share button, and hitting Save Image. (You can also select multiple pictures by tapping the Select button within a Photo Stream.)
Option two: Upload your iPhoto Library to Dropbox
If you have Dropbox or a similar cloud storage service, you can upload images from your iPhoto library and view them in that service's iOS app, then save them locally to your device.
Of course, the in-between method I would use in a heartbeat doesn't actually work: You can't currently use Apple's new cross-compatible AirDrop protocol to drop images from the Mac to an iOS device. Ah, well. Update: Looks like Mac to iOS AirDrop is working for some folks, though I still haven't gotten it to work reliably here.
Are you using the iCloud Photo Library beta, folks? Any other issues or problems you're running into that you'd like us to troubleshoot? Sound off in the comments.