Like you, I only have the freeware version of Activesky, which I still consider to be one of the best available. Beats the pants of my previous payware version of FSMeteo.

The Metar information gathered is, as far as I'm aware, the latest available via the internet. I know it's not up to the minute, but neither is it anywhere else. That's why airports have ATIS.

I honestly don't think you'd view it as a good decision to go for the payware. The FS2004 specs for on-line real weather look pretty similar to most payware packages looking at it in the long term, and in the short term, I can't see any hypothetical improvements justifying the cost.  

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I have Weathermaker and you're right, it is a great program. However it doesn't (in this version) deal with real weather, only auto-generates fictional stuff.

I got wxRE about a week ago, and have been experimenting with it.  I toyed with getting FSMeteo (which I had a few years ago and liked) but went with wxRE because it supplied visual effects (clouds, storms, etc.) to replace the default ones.  Also it has turbulance effects and good TI wake effects. Otherwise, like FSMeteo, it supplied live weather, which was important to me.  So...

I really like it.  The visual effects are sensational (no more magical cloud appearances, more realistic looking T-storms, winds aloft, etc.) and it does a wonderful job of updating my weather to real world conditions as I fly.  There is a neat 'briefing' feature that allows you to input the ICAOs of departure and destination, get the current weather and winds aloft, and plan accordingly.  Once you do this, wxRE locks in on your destination and scrolls weather updates for the location across your screen from time to time.  There is also a voice feature, which is something like the ATIS default feature in MS2k2.  It can be annoying tho, because it repeats 3-4 times before falling silent and I can turn it off (I heard you already!).  Two annoyances:  1.  You have to know how to decode METARS to interpret the flight planning briefing output (but not the local weather, which is read to you).  I read a small tutorial I found on the web. 2.  The server that updates the weather can be slow at peak times, and may have to retry.  This are really trivial tho.  On the whole, it has really been fun.  You can run it as a stand alone also, and I use it to check the actual weather (I live near an airport) sometimes for fun.  Nice manual too, very helpful with a general tutorial on weather as well as installation instructions, etc.

NOTE:  I purchased it directly from their site and saved 15$ US over what re-sellers were charging.  The transaction went smoothly.

NOTE NOTE:  It IS possible that MS will fix things in FS2k4, but I'm betting they won't enhance the clouds and weather enough to make me feel bad about the $20 I spent on this.

It's all good.  The way I started thinking about it was that, for $20, I'll enjoy it all summer, even if MS dramatically  improves the weather and I don't need it anymore in August.  At the rate I fly, I figure it costs me less than a dime a flight for the rest of the summer (until FS2k4), and I definately enjoy the enhanced effects for the time being.