AHA! Before going to a web format, one needs to check with the webmaster... oh, yea, that's me for our club :) When you are both the editor and webmaster (as in your case), the process is easier (a relative term). Sometimes the webmaster has a few tricks up his sleeve that makes conversion easier most straight forward approaches. Don't blame MS for conversion problems, blame W3C that defines the HTML standards. They are the ones who make limits on what can be done with many platforms, browsers and loaded fonts in mind. You can only come so close with HTML and a lot closer with CSS but, never the same. Also, what looks good on paper isn't necessarily good for the web. Reformatting is typically required. (don't want extra lines, font use, etc.)
Right now, I don't accept any pre-encoded HTML pages for the JCOF website for a variety of reasons. The same goes for this website too (see submission guidelines in the Library or Members areas). I have no intention of changing this policy. It is actually more work to fix and format HTML code than if it is submitted in Word or othe format.
Bottom line is that communication is required if the webmaster and editor are different people.
Some may not want to post the entire newsletter to the web. Selected items might be the preferred route for many. That is what I did while I did our club's newsletter. It was easier and quicker. Though it did miss some of the short blurbs and color photos that would have transfered nicely 'total newsletter' format.