Gillian Waldman asked me an excellent question:

Hey Torley - this may be an idiotic question but why wouldn't you just use the standard Wordpress interface on this blog (for instance) to post? I am trying to figure out why Live Writer is better. TY.

I was planning to do this followup detailing why, so, great timing.
 

The main reasons why I prefer Windows Live Writer are: 

Speed - Mostly when it comes to saving! Many times, my blog posts are compiled together from nibbles 'n' bits of ideas I have floating around. When using WordPress' own editor, saving to the server is slowwww, especially on longer posts, compared to WLW's local hard drive storage  — which effectively saves a file in a second, and without an annoying page refresh! I save and backup often, so all those little chunks add up. Browsing files locally after creating them (e.g., for editing) is also a lot faster. One performance qualm I did used to have with WLW was its slow launch time, but I just tested and this Beta 2 seems to get booted in 3 secs, so that's not too bad. Another plus is, when hyperlinking, WLW's popup window loads noticeably faster than WP's web-based one.

Style - WordPress' editor has a preview, it's true. But again, it takes a long time to refresh and isn't direct and live as… Live Writer! In WLW, I can easily go to View menu > Web Preview and get a very close representation of how my post will actually look when it's published. What's more, View menu > Web Layout also shows me a WYSIWYG view. I care a lot about context AND content, so sometimes I edit sentences or frame images a certain way based on the column width and typographical concerns (I mostly use Georgia for the body text of my blog). This type of preview is comparatively rare with blog editors (that article doesn't mention WLW), especially free ones, which brings me to…

Cost - WLW is free, which means I wasn't inhibited to try it out in addition to the standard blog editor.

Feel - Part of the great vibes I get from WLW comes from its speed and style, but in addition to that, it doesn't limit my layout or undesirably strip code like WordPress' editor does. If you like to press Shift-Enter to make multiple lines of white space like I did in this post, you may've noticed that gets stripped out in the Visual editor. Sure, you can edit finer detail in Code-only mode… but for me, that's too cluttery when I want to focus on beautiful form. (Perhaps contrary to the "Code is poetry" maxim.) And unlike pasting a styled Microsoft Word document into WP, doing things native in WLW keeps your HTML pretty streamlined and clean. In addition, while I enjoyed using Firefox's inline spell-checking for web pages like the WP editor, WLWB2 has one too. I have to redundantly add words to this dictionary since it doesn't read from the same one, but nonetheless, it's a clear improvement over not having that ability.

Image support - Yes, you can drag pictures directly from a webpage into both WP's Visual editor and WLW, but the latter is better because once you've done that, it's easier to adjust things like margin and size via sidebar options (instead of clumsily flipping back and forth between the Visual and Code tabs). You can extend WP's editor, which is based on TinyMCE, but this isn't readily accessible, nor is it as elegant a solution as WLW's intelligent choice of a compact toolbar and well-arranged ancillary options. All in all, when I quickly need to drag multiple piccies from my Flickr photostream or other sources and edit them, WLW is a lot snappier at helping me lay them out just how I want! (I hardly ever insert pictures from hard drive, almost always choosing to link to pictures already on the web.)

Management - Again, this loops in some of the above, but specifically: it's easier to get a categorized overview of pending drafts and recent posts in WLW. Helps me get a better sense of history regarding where I've been and where I'm going. WordPress' Browse ain't bad, but again, speed wins out on the local, desktop-based front. I still do comment moderation in WP's own interface, but actual writing, editing, and publishing are all done in WLW.

Multiple blogs - If you have different WordPress blogs, of course you can bookmark their Write URLs when you need to access each one. That's still slower than WLW's Weblog menu, which I regularly use to flip between Torley Lives, the Official Linden Blog, and some testing grounds.

Extensions - Plugins that help you enhance a program you already know and like rawk! I've tried a few out and didn't find them especially useful (e.g., I found it quicker to drag-and-drop than use Flickr4Writer's options), but at least I know these possibilities are open to me. There are currently 44 extensions (lucky number, hehe).

Templates - You can easily save and reuse drafts for similarly-structured purposes, as I've done for my musical Self-Review series.

 
What don't I like so much about Windows Live Writer in its current incarnation?

Integration - Obviously, since every WordPress user has the default editor, it has some advantages, one of them being that it handles Pages (non-chronological content) correctly — however, much to Microsoft's credit, Beta 2 is supposed to do pages too, so the point may be moot, and I'll have to try that out. Nonetheless, I don't see an option to set a post slug, and I don't see an easy way to download and sync previously-posted stuff on my blogs if it didn't originate in WLW. For example, when I need to edit posts made by fellow Lindens on our company blog, I resort to logging in and using the WP editor. I just learned how to open up already-published posts for editing. Joyous glee!

Cross-platform compatibility - Windows Live Writer is, obviously, only for Windows. I suppose you could run it via Boot Camp or Parallels on a Mac, but that isn't as elegant. If you use Firefox or Flock browsers on a Mac, you're in luck with the standard WP editor. Caveat: Safari, Apple's own browser, is incompatible with TinyMCE. Bleh.

Annoying screen refreshes - WLW has some odd redraw issues. Argh, as quick as the hyperlink popup comes up when I need to insert a new link, it also makes the entire editing window flicker. Refreshes also occur when editing font size, and a number of other operations. Cumulatively eyestrain-inducing!

Doesn't show the effects of certain plugins - I dig the aLinks Keyphrases plugin for automatically adding links to certain text. It also adds a distinctive pink arrow-in-box icon (which I customized from one of Google's) afterwards — but that doesn't show up in WLW. Nor does another plugin fave, Audio player, which inserts inline MP3 players when you put the word "audio:link" in square brackets. To see how those actually appear, I must publish, and sometimes the formatting isn't what I intended to be, so I quickly edit and re-publish.

"Publishing Post to Weblog" blocks you from doing anything else - For me, it typically takes 12 secs to have a post go through once I click the Publish button. In that time, I could get started on a few words in a new post, peruse my Preferences, or do other useful things.

 
Misc. observations:

• WLWB2 supports the <!–more–> tag through Format menu > Split Post. That's fab!
   
• I don't see way to strip formatting from a selected block of text. There should be a way to do that to clean up sloppy pasted input, or revert fonts to match the stylesheet's base.
   
• Looks like there's extensive support for tables — infact, a whole menu's devoted to 'em — altho I really haven't had much use for them yet.
   
• WLW also makes a nice, feature-full, yet comparatively lightweight text editor — provided you can survive with the View > Normal appearance, or at least download weblog's style you already like. Historical context: I used the previous WLW beta with the OLB style to pen many of the old Knowledge Base articles. It helped me get a lot of work done faster.

And, I've already spotted a few bugs, such as: right-clicking to add a hyperlink to misspelled text doesn't show the expected option. I've casually browsed the WLW feedback message board, and from what I've seen so far, it's encouraging to see Joe Cheng post prolifically — he's a dev on the WLW team and his status is denoted by the "MSFT" suffix. Altho he should fill in his About page to share more about his forthright self, I admire his style and I've been reading his comments across the blogosphere (that word should be in the default dictionary! *adds it*). They inspire me to continue improving communication with customers when I'm working on Second Life.

I hope that gives you, Gillian, and everyone else who's curious, more context and understanding into my reasons for enjoying Windows Live Writer. Thanx for your curiosity!