For the last six months, I’ve been working regularly on four different Macs. At home, I have a MacBook and an iMac, and at work I’ve had a MacBook Pro and an iMac. To keep the system environment similar, I’m a reluctant user of MobileMe. It has its downsides, but it’s really the simplest way to sync everything from my contacts to the icons in my dock. For some applications, I’ve noticed it will even sync your license. Authenticating the machine against MobileMe is the first step I take.

Google Chrome is my browser of choice. I trust Xmarks to keep my small selection of bookmarks in sync across browsers and across machines. My homepage is “about:blank.” Once I have my browser set up, I download Dropbox so I can start restoring my files and other application-specific preferences. As of today, my Dropbox is at 41.1%, or 21.2GB. It’s good to install Dropbox early so it can start pulling data down. Dropbox also installs Growl, a system notifications utility, which is nice because I use it for other applications.

For development, I use a combination of TextMate, Git, MAMP, Sequel Pro, Firebug, the default Mac OS X terminal, and Cyberduck. TextMate is a nice text editor with useful features for writing PHP, Python, Javascript, or HTML/CSS. I’m certainly not a power user through. Git is my new version control software of choice, and I generally use it in conjunction with GitHub. For instance, the J-School has all of our code in public repositories with multiple collaborators. MAMP takes the fuss out of running a web server on your local machine. Sequel Pro is an amazing, repeat amazing, tool for futzing with databases. Most hosting comes with phpMyAdmin. Forget that: Sequel Pro blows it out of the water. Firebug is the defacto standard for working with CSS because you can see all of your potential changes live in the browser. Lastly, Cyberduck is my go-to SFTP client. Its nicest feature for is the ability to open a file on a remote server in TextMate.

A while back, I made the switch from Gmail’s web client to Apple Mail. I love me some Gmail but Firefox kept freezing up and I’d lose my email window amongst all of my tabs. For most purposes, Apple Mail and IMAP works just fine. Contacts work out of the Address Book and you have an automatic backup copy of your correspondence. To mimic one-click archiving, I’ve installed a program called Mail Act-On.

Skype and Adium are my chat clients. Nothing too fancy there.

For reading and writing, I use Reeder and MarsEdit, respectively. Reeder is a gorgeous RSS reader that uses the reading list you already have in Google Reader. MarsEdit isn’t the greatest blogging tool in the world but it works with WordPress and gets the job done.

Last but most important: Alfred, Divvy, 1Password, and Skitch define my productivity. Alfred, an application quick launcher, makes launching any application, or finding a contact, a few keystrokes away. Alfred is also significantly faster than Quicksilver. Divvy is neat tool for resizing windows with a keystroke. I find it most handy when I start spawning too many terminal windows. 1Password handily generates a unique password anytime I’m signing up for a new account, stores them in a secure database synced via Dropbox, and lets me use the password when I need it thanks to minimal browser extensions. Skitch is absolutely what you need to communicate visually. Capture any part of your screen with a keystroke, easily annotate the image using the pop-up window, and upload the image to Skitch, Flickr, or your own server for sharing.

Fifty minutes later, I’m back in business.

I’m a big fan of services that can reliably keep my data in sync across multiple computers. Dropbox is likely my all-time favorite, and allows me to effortlessly sync 50 GB of documents, code, and media between my laptop and my desktop (ahem, .Mac). CoPress has a folder we’ve shared amongst the entire team for making accessible meeting notes, documentation, legal information, etc. Evernote, even with a mediocre user interface, enables me to quickly have access to my notes across any device. My notes are organized in the way of the GTD and I can easily search or filter by tag to get what I need.

Trust, however, is a very critical component of any relationship with a cloud or syncing service, and transparency is one method for achieving it. Dropbox is a pro in this regard; every account has at least 30 days of version history for anything that’s being synced.

Early yesterday, I made the move to Adium and decided that I finally wanted my Address Book accessible across multiple computers. Spanning Sync was the most obvious choice, as I’ve been using it to bring my calendar from iCal to Google Calendar and then to another iCal for several months now with no serious complaints. It’s blind trust in the service, though. Spanning Sync has a sync log, but the only way to revert to prior versions is to make your own backups and brute force it. The same thing applies to Address Book information which, in my situation, isn’t all that great of a solution.

I did as clean of a sync process as I could think of to get it right the first time. The Address Book on my MacBook has the gold master of my contacts, so I backed up and did a one-way sync to Google (overwriting all of my contact data) and then a one-way sync down to my desktop.

The result? I have 794 contacts on my MacBook, 743 contacts in Gmail, and 742 contacts on my iMac. It almost worked. Kinda.

Spanning Sync presents two significant issues for me that also affect the amount of trust I have in relationships with cloud syncing services in general. First and foremost, the numbers don’t add up. Not all of my contacts were synced properly, while some were entirely deleted along the way, and I have no way of figuring this out until I unsuccessfully try to find a person’s contact information. Of the 10 or so numbers marked as “favorites” on my phone, 4 lost their corresponding address cards. For the convenience of having contacts synced across computers, I’m willing to deal with this to some degree. Secondly, version history needs to be more robust than a log file. Every cloud service should keep a changelog of a week or more where the user can go back and revert an object to a prior state.

Intuitively addressing these issues in any web product means a greater amount of trust in the relationship.