I have templates on my sites, so when I fixed the main page, everything else validated as well. In hindsight though, it was a waste of time, it worked in all browser anyway

Validated HTML is easier to spider ..........

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How do spiders handle 'html' generated from word?

I recently took over managing a couple of sites and found one client that didn't like the text formating capabilities of the cms text editor so they use word, and copy and past the html into the text editor!

Put it this way, spiders can not see a page the way you look at it.
They read the source code, and if they like it, it will be stored and made available to search queries, if not they will dump it and marks the website as not important.

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Is there any software that will convert word 'html' into proper validated html?

Dreamweaver used to have a "clean up word html" option, though I'm not sure if it still does.
You could use HTML Tidy Project Page which you can run either on your desktop or directly on the server.

On a sidenote, would it be helpfult to people if I made a "spider's view" tool available?

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That would be a great idea. If nothing else, it would be interesting to compare valid against non-valid sites!

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Dont know about that, obviously using CSS files to remove formating helps but Googles smart enough to spider all sorts of HTML and I doubt cares about valid HTML. Look at the amount of errors on their own homepage! Result for http://www.google.com/ - W3C Markup Validator

Valid (X)HTML can't do you any harm of course

yep valid code is a good idea for lots of reasons, but an invalid site is far from the end of the world seo wise. since most sites are still invalid, a search engine's relevance would be seriously skewed if code validity was seen as a big deal!

googler matt cutts confirms this at Matt Cutts, Google's Gadgets Guy and i'm sure he mentioned it in one of his recent video posts as well...

but web standards is definitely the way to go - for accessibility and because they are the only known standards we have in web dev - each to their own but i can't understand how any serious web developers would argue against adhering to web standards. i mean, it's like a builder arguing for building houses that don't meet building regs! so in my book, the aim should be for each and every page to validate.

however, i agree with louie that once you hand over an editable site to a client, good luck to it ever validating again! but, a few alt tags missing here and a few pesky ampersands there is not a big deal... there is a big difference between sites that only have a few minor errors and code a la microsoft word's web page wizard!

As far as i know - Most people use "Templates" in one format or another. Either its a DWT in Dreamweaver or a Notepad edited page - If not you should, your mad not to !

I would recommend validating all pages during development of each page type. Here is my recommendation...

1. Build and Test the Site Template (if you use templates - if not test a page with no "main content").
   Once you have a valid template you can be fairly sure your Basic Pages will validate.
2. Build and Test the Basic Page (About Us, Resources etc)
   As these pages tend to have more text than anything else, it makes sense to validate these pages next.
3. Build and Test the Product/Services Detail page
   Once your basic page is up to scratch, i would suggest building one product/service detail page and then test it. Once this page has passed, you can go ahead and build the other detail pages. This helps fix your code before you replicate the page to build other detail pages.
4. Build and Test the Product/Services Main pages
   These pages tend to have more varying elements, and require a little bit of additional work. Again build one and test. Once it meets the standards, use this to build the other main pages.
5. Build and Test the Home page
   The homepage is the cover on the book - always leave it to last !
   The homepage always requires more work in terms of graphics, text, layout etc, and therefor the markup is likely to be extensive. For this reason i would do the homepage last.

Basically, consider the structure of your site. Look at pages that will be similar (template, product or service details pages, product or service main pages, unique pages like the homepage, contact page, special offers pages, news page etc).

I have developed many sites to W3C standards and Accessibility standards, and over time have found the production shortcuts that work for me.

The last thing you should do is build a wall and then check to see if it is level when you are finished. It is easier to fix a problem at the "source" (excuse the pun, ....no ....DONT ) then when the site is polished !

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If your client intends to edit the content and keep the site up to the markup standards, i would look into the Dreamweaver + Contribute combo. DW8 writes fairly clean markup (and some extentions clean up any missed by DW), and contribute SHOULD do likewise. I have recommended Contribute in the past to clients, but not for a while and have no idea where it stands on compliance to W3C standards. - worth a look all the same.
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I decided to make a bit of a contribution as i have started 2 threads looking for advice, and feel its time to give a little bit back....
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- Meanö