I am an email freak. There, I have said it. Email was one of the first services I got into when I first got on the internet. For what seems like forever, I have been trying to figure out what email system to use. In a perfect world, I would be running my own mail server here at the house. I used to do that as a matter of fact. When I had DSL, I ran my own Exchange server here at the house. Then I switched over to Comcast for my ISP. I started noticing that my emails were getting blacklisted when I tried to send them to people. Come to find out only the IP's for the authorized Comcast email servers are good to go. Because of issues with DSL, it wasn't possible to go back. I also have two domains that I use for my email, so I am not tied to any email option as I can easily point my domain email to whatever provider(s) I want.
My email needs are fairly straightforward. I use it here on my workstation at home, my work laptop, and my workstation at work. I use both web email and email clients like Mozialla's Thunderbird and the Windows Live Mail desktop client. I also connect via IMAP with my smartphone and have it sync every 5 minutes.
The Comcast email services sucked hard, so that wasn't option and still isn't an option.
GMail
About the same time I lost the ability to roll my own mail service, Google came out with its GMail service. It has been pretty good for the most part. I have had it die on me a few times and have had weird bouts of tons of SPAM filling up my inbox. Lately, I have seen some lag in my service. Nothing too bad, but noticeable. I really don't care for the ads, but I am too cheap to do the full version of GMail Apps and don't need all the features. Sometimes Google just freaks me out. They know too much about me. They might be good with my info, but what happens if they are ever compromised? They do have a little of interesting features and there is a lot of community support around the service which makes for some interesting ways to check your email.
Hotmail/Live Mail
I have had a Hotmail account since before Microsoft purchased the company (remember 2MB caps on your email storage?). Honestly I have not had any issues with Hotmail. It has pretty much worked like it should. A few false positives with good email going to the SPAM folder, but not too bad. The only downside is that it is $20 a year. I don't like looking at the ads and having the ad tagline going out in my email on the free version. I don't care for the proprietary nature of Hotmail. They don't open it up to POP or IMAP clients. Their site also reverts to a "classic" version in Firefox. Fine when I am running Firefox on Windows as there is the IE tab option, but not so great if I am running linux which I do use on occasion. I have been using a free promotional account for the last year which makes it kind of hard to let go of the paid service.
Yahoo Mail
I have tried a year of Yahoo Mail and I didn't like it much at all. No IMAP means no real access on my smartphone. POP is OK, but again it costs $20 a year. Yahoo to me is a mess with how their SPAM filters work. I also had significant delays in my emails both arriving and being sent out. To me, this one isn't a contender.
Inbox.com
This one has a pretty slick web interface. They used to have a 5GB for $10 a year plan, but they don't have that anymore. They also don't have IMAP which again is pretty much a necessity. They allow POP, but after using IMAP, you just don't want to go back.
FastMail.fm
I purchased a subscription last year for FastMail's enhanced account. The reason for it is that I was working with someone overseas that we would need to send large files and executable files back and forth (since then things like dropbox and Windows skydrive allow for easier file sharing) . GMail and Hotmail don't allow this (and neither do many email providers), but Fastmail does. They aren't cheap. $40 a year for the enhanced account, but since I paid for 4 years in advance, it brought it down to about $23 a year. They have so far been a pretty good service. IMAP, custom whitelisting of email addresses, plus many more features. Their web email looks kind of like something straight from 1993, but it works. There are plans to get this upgraded soon. The biggest shortcoming with fastmail is the price.
I have tried a few other smaller providers and they weren't very good (GMX Mail, Lavabit). Right now I am a bit undecided between GMail, Live Mail, and FastMail. They all have their pluses and negatives. GMail is pretty good, but it just has enough quirks to make me wonder about using it (I don't really care for how the messages stack up like index cards in a recipe folder. Perpetual beta?, what is up with that?). Hotmail makes me think it is too proprietary, but it is a solid service. Fastmail is spendy, but has some great attributes and I am paid up until Nov 2011. Time to mull it over a bit more to see which way I want to go here.