... So this is also a reuniting with Apple after about 15 years. But hey, if the G3 works and gets me to where I'm going everyday... It'll be all good for a while anyhow.
New start after 15 years ... Well, with the iBookG3 you really start at the point where you left - good timing!
As others stated before: I'd go with Tiger too because of TFF support and because it's the latest OS X that will run on that machine.
I don't know much about music-related software but I think Dronecatcher is the one who can tell you most about it and going back to os9 with dual-boot-option into os9 and Tiger is the way I'd go too.
As Dronecatcher mentioned macos9lives.com is a very nice community and everything there is about os9 and music.
For my part I was pretty amazed about os9, when I tried out to get the max out of my Clamshell G3 with dual-boot option of os9 and Tiger.
You may also get access to the os9 partition by using Classic-mode of Tiger.
When it comes to the Cloud or Contact and Calendar-Sync etc the iBookG3 really falls a bit short:
- forget about Dropbox, iCloud, GoogleDrive, OneDrive or Apple-Calendar/Contact-sync with your Android-phone. It doesn't work or will drive you nuts! The only reasonable way using the cloud is via webdav e.g. with box.com. You can access webDAV with Tiger via Goto/ConnectToServer without any additional means. For os9 use 'Goliath'. Last thing I found out, that Office2008 offers a nice OneDrive-Client with it's 'DocumentConnection' but no Sync like Dropbox offers
- FileSharing: it's possible to connect os9 to Tiger/Leopard and vice versa
- email: native MailApp of Tiger or mail-client of Classilla (os9)
- iTunes 9.1.1 is the latest version and may connect to local iTunes libraries and may play internet-radio but nothing more.
- iPhoto: you may not succeed to sync fotos of your smartphone. At least the latest iOS-versions do not support Tiger/Leopard/PPC anymore.
- WLAN: you'll need e.g. an EDIMAX USB WLAN-stick for the latest security-standards. It does only work with Tiger/Leopard but not with os9. WLAN-workarounds for os9 are a bit clumsy if you don't want to downgrade your WLAN-security ('"ASUS 3G MOBILE Wireless Router (WL-330N3G)"). Another drawback: any USB-WLAN-stick will run through the bottleneck of USB1.1 (so that clumsy workaround, that connects to the ethernet-port is a much faster option!)
Here's some more info about my os9-clamshell-experience and all the advise I've got from the people here!:
https://forums.macrumors.com/threads/email-client-and-applications-for-mac-os9.1960993/
Cheers and have fun!
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There's Busycal (which I use ) and now I can't remember the other or was that SyncMate
I tried to use ChronoSync for Syncing a local folder with webDAV but it proofed to be not reliable and really really slow.
Any substitutes for that purpose?