Hey guys! Long time lurker, first time poster. I've done a LOT of research on this and searched through the forums. Some threads dated back a bit, and I figured with my unique situation and previous tech knowledge, some might have some different insight for me. So I'm pretty tech savvy, but my knowledge in the Apple department is not booming as my knowledge with Windows based devices. My love for Apple started 2 years ago when I got my first iOS device - the iPhone 4s. I know own a mac mini, iPhone 5s and a iPad Retina. Love them all, and looking to get rid of all my windows based devices. But I'm not here for me, I'm here for my girlfriend. So here's the story. She has a MacBook Pro 2011 and is a photographer. It is currently bone stock. since buying it, she has kept all data on her Mac as well as backing up all files manually via drag and drop on an external hard drive. Well, she had been saying it's been getting slow and frustrating, so I got her a 250gb SDD and 8gb of ram for Christmas. Well, I still haven't upgraded her because she hasn't given me the time of day (insert sex joke here). Well, as of yesterday, she finally has everything backed up and I'm ready to upgrade her. Now, since her SDD is going to be smaller, I told her she isn't going to be able to keep all her media on her computer all the time, and that she is going to have to be good about doing backups. My plan is this. I'm going to take out her hard drive (500gb) and throw it into a USB 3.0 enclosure. She already has a 1tb external as well, so she'll have 2. I told her being a photographer and owning a business meant you needed to have 3 backups of your stuff at all times. However, I'm just trying to get away with 2 for her right now. If I talk about nerdy things for longer than 3 minutes she loses interest and starts picking her nose, so I gotta start small and work my way up. Right now, her plan is when she needs to backup, plug in one drive and drag and drop, remove it - plug in the other drive, drag and drop, then call it a day. Well, being a lover of increasing productivity time, I told her that was a waste of time and she will get sick of doing that very, very fast. And in the off chance you forget to backup to one, and that drive goes, you're going to lose your stuff. So, I'm trying to find a backup solution for her that is simple and redundant. I'm not worried about off site backup at the moment, because she leaves one drive at home and one drive at work. I'll set her up with CrashPlan or something later on. One article I found online showed a photographer had two portable external hard drives rubber banded together, he would plug then in at the same time, and he ran some type of command to backup her things to both drives at the same time - so that the drives were identical. So I started looking for options. At my house, I use a 8 bay Drobo Pro to backup my media server. I automate backups with SyncToy. Every night at 3am, SyncToy runs and backups all my drives to the drobo. When a drive in drobo dies, I just replace it - it rebuilds the array and it's done. Simple and awesome. However, that is a Windows based machine. Although I love my Drobo, I have read a lot of bad things about catastrophic failure, and people losing a lot of data when the unit fails. That can't happen. So I'm ruling out drobo. For my media center, I know it's not a huge deal because if the drobo dies, there is nothing on the drobo that I don't have on the server. However, since my girlfriend will only have things in one place on the drobo, that cant work. Now, I have read much better things about Synology - but i run into the same issue. What if that single device with multiple drives dies and she loses everything. That would suck. Now TimeMachine and Time Capsusles are another option. I've read in a few places that you can attach an external hard drive to a time capsule and create a redundant backup. However, I have not read reviews on how well this works. so i'm a little weary about it. I've always wanted to try a Time Capsule, but never have. So what do you guys think? I would greatly appreciate some advice. The idea in my head that I have right now is for her to have 2 separate external hard drives, and be able to plug them both in, and run a program like SyncToy that can just take all the content in the folders you specify and move them to both externals. For those who don't know how SyncToy for windows works, it basically a tool that says "Tell me what you want to copy off drive A, and I'll move it to drive B". As you can see here, I have a 'folder pair' assigned for each hard drive. So I have folder A, B and C on my server, and I created folder A, B and C on the drobo. Whatever content is on the abc folders on the left is put into the abc folder on the right. Super easy and simple and I love it. So basically how I'd like this to work is if she plugged in both hard drives, I could just say "Mac, take everything in her user folder off C: drive and put it in Backup Folder on drive 1 and on Drive 2". Is there something like SyncToy for the mac? I came across an app called Super Duper that looks like it does the same thing, but I just found it and haven't read much about it. So should I have her drop some money on a dual bay synology NAS with RAID capabilities? So if a drive dies I can just swap it out? And maybe get a 3tb external with auto backup as a secondary backup? Maybe have the 3tb Western Digital be a Time Machine backup that backs up wirelessly...Maybe i'll get her a Time Capsule for her birthday since she needs a new router soon anyways. I'm just mainly concerned about her pictures. Although she has some music, she streams all media from my home server. And it's gotta be automated because she'll forget to backup. So after the upgrade, she'll have a MacBook Pro with 250gb SSD. She'll have 1 external hard drive that is 500gb, and her new external she just bought that is 1tb. If i find her a better solution I'll just buy it off her. What do you guys think?