Let me start this post by saying that without Macrumors I would've been and may still be a little lost since moving completely from Windows to Mac over 5 years ago. Maybe you think I'm kissing butt because of what I'm typing below but I'm not. I'm a true Apple fanboy now and tell EVERYONE who ever asks me how to do something to start here. I'm 35 years old and couldn't do much more than e-mail 7 years ago. 2 real years on a PC and the last 5+ on a Mac has made me more money in my business and I love working on these machines and learning how to do things that I never though I could do on my own. With that being said here's my issue... I want to merge 2 Macs into 1. My main machine for every day use is a 27" iMac with Lion. It's the only one I synch my iPhone with, have all my passwords saved in, all paid apps/programs installed. My secondary machine is a White Unibody MacBook. When I bought it I primarily used it at home and on the go. What I want to do is clean out and sell my iMac as I am not using it and can still get a pretty penny for it. My main concerns are; 1. Merging Mail from the iMac to the MacBook. Both have been used recently so there are important e-mails on both (a couple thousand on each) 2. Moving my iTunes library over. 3. Being able to synch my iPhone without losing anything to my MacBook instead of my iMac 4. IMac has a 1TB HD (only 250 gigs used) moving all needed files to MacBook (only 500 gig hard drive) I know that there is 75 % overlap in files because initially I dropped them into the MacBook for iMac when I purchased it. I have current Time Machine back ups of both. I'm not worried about losing the data, but merging it seamlessly to keep my workflow smooth. I'm really worried about merging both Mail files as I've been through the pain of having to look through archive files imported to Mail from Entourage and Outlook and I never remember where to look. Obviously you shouldn't use e-mail as a pseudo file server but I'm flawed like that I'm not worried about paying someone a couple hundred bucks to do this work but I just don't trust others to get things done right. I love Apple but had 40-50 hours invested at the Apple Store years back when there was a synching issue between my MBP, iPhone, and Mobile Me. If Geniuses can't future stuff out always, who can you count on? Here's a slim rundown of each machines specs; 27" iMac 8gb ram 1 TB HD Lion OS 1TB external with Time Machine back ups Unibody MacBook 8gb ram 500 GB HD Lion OS 500 GB external with Time Machine back ups All thoughts, directions, and warnings are more than welcome.