Procrastinating on configuring a private email server on Amazon (Postfix, Dovecot, SSL, ClamAV, SpamAssassin): 6 months.
Moving 70 000 emails from 6 accounts (3 Google Apps, 1 Gmail, 2 other), reconfiguring MX, DKIM and SPF for own domains: 1 evening.
I wanted to get off Gmail for a long time. The first move was to Google Apps, it worked pretty well, but it was the same server underneath. I almost never use the web interface, so IMAP functionality is pretty important. Gmail's is... well... let's say, peculiar at least.
Recently Gmail IMAP really got worse, not hypothetically. Deleted spam messages started popping back again, a few Sent folders appeared for no apparent reason, all while I was using the same client. It wasn't frustrating per se, but I got tired of that. Also using four Gmail accounts at the same time (3 Google Apps for my own domains and 1 Gmail account) is not very convenient when there are a ton of labels in each one.
The solution was to unite all these accounts and create a unified inbox, which would be easy to navigate and fast to use. First, I wanted to just larch the messages from my Gmail and other Google Apps accounts into my main Google Apps account, the one on this domain. For some reason this did not seem like a good idea: if something went wrong, it would be pretty difficult to decouple the accounts and put everything back together. I'm a sysadmin, so Branson's famous “screw it, let's do it” isn't something I do often. You don't rush things when there's a possibility that you'll have hundreds of people unable to work for a few hours. Better spend two days of your own time on a problem and do everything smoothly. Well, you get my drift.
In the end I settled on rolling my own server, there are plenty of manuals around. Keywords are Postfix and Dovecot, those are two key components to the setup: Postfix gets mail and Dovecot lets you read it. All the other parts are more or less optional and depend on personal preference. I compiled my own best config and set out to do this a little later: I just left my job and had a few short months ahead to learn a new occupation.
Fast forward six months, the private server is still on my monthly to-do list, but I don't have that much free time to spend a couple of days configuring it. Gmail, after all, isn't the worst mail server. A few days ago I stumbled upon a discussion (which is private, sorry guys), where someone mentioned FastMail. I read up on them, and they have a pretty interesting history. Just recently the company bought itself back from Opera so that they could continue running their email, clearly they care for their customers a lot.
Actually, the FastMail/Gmail thing reminded me of App.net, which is, in a nutshell, a user-supported completely ad-free version of Twitter. It's the same with FastMail: because it is not a free service, they can really care for their customers, and the customers love them back. I know I do. Just using their email for a few hours shows how much they care, and it gets me every time.
But let's get back to the point. FastMail offers a 60-day trial, virtual domains and IMAP migrations, all of which are necessary for me to a) try out their service b) get my domains over to them and c) get my email into FastMail. All of which I did, spending just a couple of (active) hours. Finding a service that is actually user-centered, compared to Google, and offers custom everything out of the box instantly seemed a no-brainer for me to run with that instead of spending my time on rolling my own solution.
In the end, that is a question of priorities. For me, having full control over my email is of less priority than having a single mailbox that lets me write from any associated email address and also collects email from all my other accounts that I don't actively use. I'm not afraid of someone screening my email because I'm not a criminal. Still, FastMail let me make another step to independence: now instead of six accounts I only have three, one being FastMail and actively used and others just forwarding email just like they were to Gmail before.
Next steps: keep a synced and backed up local copy of the whole mailbox with offlineimap, which can easily be uploaded to a private server if I ever have one, because there's only one active account now and because I'm using my own domain instead of a @gmail.com address. Just set up the server, upload email, change MX and off you go.
You know why it's called FastMail? It does work really fast.