1) Easy, unsecure, synchronized, stored everywhere mail. 

For this I’ll use Apple’s iCloud. While it doesn’t work great at this time, it is an ideal solution to keep all the non-sensitive stuff synchronized between all devices.

2) Secure E-mail.

For secure e-mail I’m going to setup an Amazon EC2 instance. On this instance I’m going to be running NetBSD with an encrypted filesystem to store the mail

The primary means of accessing the mailstore on this machine is going to be via ‘pine’, a small, easy to use, text based email client.

<edit next day>

I ended up using netbsd instead of ubuntu. I’m using netbsd’s default email setup, then encrypting the home dirs (so that the email is stored encrypted), and using pine to access the email (so its easy to access and use).

On freeway during rush hour.

Very poor push functionality
Only the inbox of my iCloud account actually notifies me of new messages.

For example if I have a folder called travel and a rule in the web mail client at iCloud.com setup to move mail to that folder when the sender is say aa.com. The mail is properly moved, but I receive no notification until I refresh the mail client on iPhone. This is a major deal killer:

In addition to no notifications outside of the primary inbox, even the inbox notifications are inonsistent, sometimes requiring me to manually force quit the mail app on iPhone an relaunch it to get push functionality again (this causes hours of missed emails as sometimes I won’t notice right away it’s not working properly).

I’ve had a mobile email device since u2k (palm 7). And have had instant email notification via SMS/mms since 2001. I don’t understand why now in 2k12 it has less consistent functionality.

junk mail
iCloud’s junk email system sucks. It provides little ability to configure it, and in general doesn’t seem to smart. It never seems to learn from me.

Mail rules
I get a lot of email, around 70-100 emails a day. Many of these are for reference purposes only and just need to be filed away (invoices, receipts, bank statements, dividend summaries, etc). If they are all left in my inbox I have a few problems:

1) Too much mail in the inbox. Makes it hard to find anything and inefficient in general. Best email practices usually dictate that the inbox should be kept small, so that it’s easy to see what remains to be done, this I need the majority of my mail sorted into other directories.

With exchange, the list of rules is stored on the exchange server and synchronized rule management either via web interface, os x client, Linux client, or the windows client. So no matter where I set up a rule I can view and manage it from any other client.

With iCloud if I setup rules in the osx mail.app on my laptop, they would only be enforced when my laptop is plugged in, powered on, connected to the Internet and bad the mail.app actively running. This is horribly implemented. When I apply rules via the iCloud web interface, they do run all the time, but as mentioned earlier they mess up the push notifications.

no categorization
I like how in exchange/outlook I can go through and categorize my contacts. This way if I just want to see work email I can click the work category and everything else is filtered out.

In addition in my inbox mail from different categories shows up in different colors. This way with one glance I can tell of there’s anything work related or really important. These categories seamlessly integrated with the blackberry + bes + exchange.

Come on apple get it together. Stop playing with your customized, half broken version of IMAP and take a lead from Microsoft exchange and blackberry enterprise services. I understand your not targeting corporate users, but still the current email situation often makes me wish I still had my blackberry.

The AMEX Travel App also has great TripIt synchronization and I prefer it over the traditional TripIt App because it condenses previous flights and such, so if your on the 10th flight of a 15 flight trip, you don’t have to scroll past all the others first (which is incredibly annoying in the normal TripIt application, especially if your on a really long trip).

This is actually one of my biggest problems with the normal TripIt application is that it shows all your previous travels on your trip as well, which can be alot more information than is needed or wanted, and takes forever to scroll past. I wish by default it would scroll to where the next flight or whatever is as opposed to just starting at the beginning.

The points tracking feature of TripIt Pro is alright, though I prefer AwardWallet Plus, which lets met track not only my accounts but also all those of my family (and really anyone else if wanted).

TripIt is great software though, it recognizes 99% of the travel plans that I forward to plans@tripit.com, the iCal feed works great, putting all my travel plans on my blackberry as well as desktop/laptop and icloud.com.

http://www.tripit.com

I just wanted to post a quick note for anyone else looking for gallery software that menalto’s gallery software is great.

http://gallery.menalto.com/

You can view an example at my gallery @ http://gallery.cheezy.com/

CrashPlan is great in theory, however there are a few issues:

1. The software (GUI) itself is slow on all platforms I’ve tested it on. The free version also offers no control over compression or encryption (though backups are encrypted and compressed according to documentation – even in the free version).
2. The daemon seems to take up more resources than I want it to. Maybe its just me, I don’t like java.
3. I prefer to control the encryption myself.