Request for tech help: reward offered! The .PST -> Gmail move

I am finally going to take a step I've contemplated for quite a while. I have at least a dozen years' worth of correspondence piled up in my old, archived .PST files for Outlook, and I am ready to move all of that into a Gmail "cloud" account.

For the record, here's why I think it's time to take the step. I lay this out for anyone considering a similar move:

- Affordability. As mentioned earlier, Google has made available essentially limitless amounts of online storage for very low prices. Its announcement here; my earlier comment on it here; price schedule here. I'm currently signed up for an extra 20GB of storage, on top of the 7+GB that comes free with each Gmail account, for $5 a year.

- Convenience. It's inevitable that every year or two I'll migrate from one computer to the next. I would rather not have to worry about migrating, preserving, updating, etc those physical .PST files each time. Google has its pluses and minuses, but I assume that its engineers are more professionally competent at storing and protecting information than I am. Is there a risk that somehow they'll lose it all? Perhaps. Statistically there is a greater risk that I will (because of theft or fire, because of aging media, etc). Is there a risk that they'll spy on it? Maybe, but I have bigger worries in life. And after all, every email I've ever sent or received has passed through systems that scanned it for spam etc, so it's already been "surveilled" -- like everything else we do on line. (Topic for another day.)

- More convenience. I keep most of my research and working files up-to-date among my various computers via cloud synchronization with SugarSync. The huge exception is Outlook files. For reasons mentioned below, they just won't work with most online sync programs. So I have to copy them over one by one via USB stick. If all the archives lived in Gmail, I wouldn't need to do this. All my computers would always be up to date.

- Searchability. The main reason I want to have those old files is to be able to search them, when needed. It's faster and more flexible to search within the Google cloud than it is on my own machine. (Inside-baseball point below.*)

- Cumbersome nature of Outlook. That Outlook works as well as it does is impressive -- it has been years since I've actually lost information from it. But it's the most crash-prone of Windows programs I regularly use. Also it seems inherently cumbersome. For example: If you want the contents of old .PST files to be searchable within Outlook, they all have to be "open" each time you use the program -- and every single one of the .PST files is then marked as having been "changed" merely by virtue of being opened, whether or not a single byte has been altered. That is a nightmare for any backup or archive system. Even if you have not written, deleted, or read a single message, simply by loading Outlook you mark all open .PST files as newly in need of backup, which creates a practically endless loop of needless backup chores.

- Mac tropism. Two years after annoyance with Vista led me to get my first Mac in many years, I've bought two more and shifted my computer-world center of gravity to the Mac platform. The shift is partly to Mac-only programs (notably Scrivener, also DevonThink) but mostly to platform-agnostic ones -- Personal Brain, MindManager, and of course all Web-based apps. I still always run WindowsXP under VMWare Fusion to use favorites like Zoot (out soon in entirely new version) and others. But, well as Fusion works, running an operating system (in this case XP) in an emulator, under another OS (in this case Mac) is inherently inefficient. And Outlook seems notably to slow the system down. I use Outlook only for email -- have migrated all calendar and contact info to the cloud -- and so if I could have my email archives live elsewhere, I wouldn't need to run Outlook any more.

So here is the challenge: Who knows a step 1-2-3 automated way to get a large number of old .PST files moved into a Gmail account?  The biggest of my Outlook files is about 700MB; I have many, many of them, so I need a way I can do this through some kind of automated routine.

I will collect suggested answers; give them a try; and share here the two or three approaches that seem to work best. Also, will give (a) multi-year Atlantic subscriptions and (b) your choice of book or books by Atlantic-family authors to the deserving winners. Being vague about this because I'll adjust prizes to the wishes of the winners -- and how good the advice is!

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* Inside baseball: the Windows search application X1 is a phenomenally fast, flexible, and accurate indexer of .PST files along with most anything else on a Windows system. It's in an entirely different league from the built-in Outlook search system. Unfortunately, in handling .PSTs it inherits what I described as Outlook's clumsiness. It will only index and search .PST files if they are "open" under Outlook -- and opening means that all of them are constantly marked as having been "changed" and needing backup. If I am wrong in this understanding of X1, I will welcome that news -- which might allow me to use Outlook in a more streamlined and sustainable fashion. It would keep "open" only the file for current activity, but I could still find old correspondence with X1. But I don't think that's how it works.