Upgrade now (directly from 10.6.8) to Mavericks 10.9.5, to Yosemite 10.10.0, or wait for Yosemite 10.10.x? My OS X Upgrade Dilemma… I have downloaded the 10.9.5 Mavericks installer last week. I am experiencing some iCloud envy… still running Snow Leopard on my MBP… Should I upgrade to Mavericks 10.9.x now, to Yosemite 10.10.0, or wait for Yosemite to mature at v. 10.10.1? I usually wait for x.y.z (plus a week or two) rather than using any x.y.0 software. (Especially after the recent iOS 8.0 to 8.0.1 to 8.0.2 to 8.1 fiascoes...) :: My Hardware :: I have a MacBook Pro (MacBookPro5,4 — 2.53 GHz Core 2 Duo, vintage 2010) that I bought via Craigslist (with a few scratches on the case) a few years ago at a steal. Also using an iPad Air with iOS 8.0.2 (128 GB, Verizon) for 50% of my work… and the old MBP for the other 50% of my work. I have upgraded the MPB to 8GB of RAM and installed a new 1TB (7200 RPM) hard drive last year. I am willing to make a clone of my 1TB internal hard drive and then do a clean install... I also have a time machine backup on an external 2TB drive. :: My Software :: Still about 90% happy with Mac OS X 10.6.8 here… but I have some iCloud envy. Still using the old GraphicConverter v. 6.7.4 from 2010. It can do about 95% of what I need, and I don't want to go thru a day or two of learning curve on a piece of software that I have been using (on every Mac I ever owned) for more than 20 years. Bought Microsoft Office:Mac 2011 but have yet to install it. Still running Office 2004 (Excel, Word mostly) which does about 95% of everytning that I need to do. I have VMWare Fusion (5.0.3) and WinXP and Win7 but very, very rarely use them. About 60% of what I need to do is web-based, and almost any platform will do. iPad, Mac, or whatever… (I do often switch back and forth from MBP to iPad - and I rely on things like Evernote and Google Drive and iCloud to coordinate…) Should I upgrade now, directly from 10.6.8 to Mavericks 10.9.5, or wait for Yosemite 10.10.x? Will the advantages of all the iCloud integration make it worth the cost and the pain of upgrading? :: Bottom line :: What software that I am running now will not work on Mavericks, OR on Yosemite? How to determine that? Is there an app for that? What will the upgrade cost me in time and money and inconvenience? Will the pleasure be worth the pain?