I too was a long time DOS and Win user. I'm really not seeing the problems you are having, other than the disappointment with Quicken. I use Outlook at work and Mail at home. I have both business and personal emails on both. My calendars are all linked as well as my contacts. I freely move files back and forth from Word and Excel to Numbers and Pages. Both are sync'd with my android phone. I also use remote desktop from PC to Mac and back. To be honest, even QMac has been more than adequate, just not as pretty. I still save all my photos in a folder, categorized the way I want and I only import them to iPhoto or iMovie when I want to manipulate them. The upside is, after 4 years, the Mac has locked up less than my new at work Dell XPS Win 7 PC did in the 1st 3 mo. I will buy another Mac when the time comes, but the way it is running now, it may be a while.