Moving from (or integrating) Outlook, Android, & the cloud

Something I’ve been trying to figure out for a while, but Googling hasn’t really helped much – I’m finding explanations that don’t quite fit my situation. Advice, thoughts, and in particular experiences are welcome.

I have my own domain, and hence my own domained email, which pre-dates the days of Gmail being freely available so I was long-established in using Outlook at home for my email client well before popping email into the Gmail interface was a thing. I also use Outlook calendar and tasks heavily – they are indispensable in how I organize and track work, bills, etc.

I do not currently have a smartphone, but will need one eventually as my phone is pretty old. When I move to a smartphone, I would like to be able to integrate the phone with my calendar and tasks as well as email.

I’ve also put some thought into moving my email to the cloud via popping into Gmail and using that exclusively as my email client. The advantages are obvious, particularly concerning needing to backup/move email from one computer to another as my equipment ages. Where I’m getting stuck is that I would need to somehow move my existing email, and some of the archived email, from Outlook to Gmail, including creating labels that correspond to existing folders; along with calendar and tasks. I can’t seem to find a way to do this – what I have found via Google seems to be geared for Outlook Exchange or Google Apps, neither of which apply here. I need to find old emails often enough that it would be a significant disadvantage not to have them on hand – I often have work projects that span weeks or months and need to go back to old emails to refresh myself on what the client needs.

The other question is whether Gmail has the calendar and task functionality that I need to keep myself organized. If I don’t have task and calendar reminders popping up, I WILL forget things; I’ve got too much going on. I like the Outlook reminder pop-up, though I imagine I could adapt to getting reminders in my email – but can you “snooze” reminders and get another one in an hour or a day?

However, if I stick with Outlook, is there a simple way to sync the calendar, tasks, and email with an Android phone directly? (Currently using Outlook 2007.)

So, has anyone managed to move email from your local computer / Outlook into Gmail? Do you use Google Calendar and Tasks and are you happy with how they function? Can you “snooze” events or task reminders? Is there a way to “flag” email you receive and set a reminder to deal with it at some future time?

Or is there a simple way of syncing Outlook with Android (and possibly syncing Outlook with Gmail)?

Between the two options, which do / would you prefer?

Bonus question: what are your thoughts of Google Voice and how it integrates with your smartphone?

Please keep in mind while I’m pretty tech savvy for a user, I am most definitely not an IT specialist. If your answers rely on tech jargon or buzzwords, odds are slim that I will understand you.

Thanks.

ETA: I do have an existing Google account which links my G+, YouTube, Docs; but I have not yet activated Gmail on this account. If/when I move my email to the cloud, this is the account I would be using for Gmail, calendar, and everything else. It is not a Google Apps account, though I’m not sure what the difference between an ordinary account and an Apps account is.

Bump. Any thoughts, opinions, experiences, personal preferences… ?