Choosing The Most Reliable Email Option

Today, Claire asks:

I just stumbled upon your blog while googling for info about my current email problems, and in reading the various Q&As realized you could be a great source of advice for me.  This may be a bit more general of a situation than what you’ve featured on your blog – but I thought I’d email anyway and see if you had any thoughts.

So my main question is, in your opinion, which is the most reliable free email service?  I can’t seem to find any definitive data on that anywhere, just anecdotes that would make it appear every service is terrible.  I also can’t decide if I want to use a program to access my mail most of the time, or just stick with webmail, but in any case I want to do regular backups since I no longer have something like the AOL program storing emails locally.  What would you recommend in terms of programs for mac OS X (currently 10.4 but hopefully upgrading to leopard soon)?

I’ve been an AOL user for many years, using AOL’s program for mac OS X and more recently the webmail also (I’m a bit confused as to how those two work together – a lot of my recent emails aren’t appearing in the program’s “filing cabinet” since I’ve been using webmail increasingly – but I suppose that’s another question).  In the last few months I’ve had problems with emails, both incoming and outgoing, randomly getting lost with no error messages sent to either party.  So I decided the time has finally come to switch to another email service.  I’d heard good things about gmail, so I set up a gmail account and tried it out by routing all my AOL mail through it using POP (just temporarily, to decide if I like it).  It’s working fine, but I’m not sure gmail is the way to go for me – several things about it just bug me, and in reading the complaints on the google support boards it would appear the reliability isn’t much better than AOL.  

The main things I dislike about gmail are the threaded “conversations” and the handling of contacts – I’d really just like to see the email address an email was sent from, not the name of the person (and I’m not even entirely sure where most of the names come from – they’re not named in my contacts list, so it must be something coming from the sender, but it really bugs me there’s no way to turn that off and just see the email addresses).
One other detail – I’m going to college in the fall, and the school has just started using Zimbra for email.  I couldn’t use that email address as my primary email for a number of reasons, but the little I’ve looked at it so far I really like the interface, so maybe it would make sense to route another email address to that webmail interface (POP? forwarding?).  I also saw on the Zimbra website something about a Zimbra program, but I don’t know if it’s a paid thing or if my school supports it or anything.  

So given all this, what would you recommend for my email setup?
And one more issue – I have years worth of emails stored up in the AOL program, which in theory can be imported into Apple Mail through the AOL service assistant, but which always mysteriously results in a few hundred less emails than I started with.  I’ve recently found a new route out of AOL, through the AOL Desktop for Mac beta program, which lets me import the old emails – then they’re stuck in that program, again no export feature, but they’re now apparently saved as a .sql file, which I’m hoping can be somehow converted to a .mbox or something – still trying to figure that out too, suggestions would be greatly appreciated!

Thank you in advance for any advice you can give me – I’m sorry this is so long, I was just thrilled to find a person who might be able to help me with this situation! 

After a mishap with Gmail due to it apparently not being all that difficult to hack into, I have a difficult time recommending anything that you are not in direct control of. This means in a perfect world, you purchase a domain name and setup an email hosting account from there with a good Web host. That is my strongest suggestion, be it not the most practical for most people.

If this is not viable, you can look into Yahoo mail, just make sure you are using it with HTTPS in the address bar. This will ensure that you are not sending your login information in an insecure manner. As for Zimbra, I think that using the website based interface is going to be the best bet for you. This will provide the path of least resistance.

And finally on the imported email note – it is anyone’s ball game to be frank. AOL has managed to make migration a 50/50 proposition. I am amazed that you had as much success as you did thus far. AOL is notoriously difficult to migrate away from. So I am going to have lean to the community for additional ideas of what might work – Gnomies, any thoughts on salvaging her old AOL mail that might actually produce results?

Do you have an IT-related question? Perhaps you are just burnt out on writing on the walls with crayons? Whatever the comments may be, drop me a line, and you too can “Just Ask Matt!” Please address comments to the comments section above, my email address is for questions – thanks!