Forum OpenACS Q&A: Re: Windows - OpenACS and AOL server - Help Getting started
Also, Jamie did not necessarily write up everything you need to know about running OpenACS on Windows. He has said himself that even the newer version of his docs are not entirely complete. If you use his old compiled binaries of everything, his info is likely to have everything you need. However, if you need anything that's not there though (like say the latest bug-fixed version of nsopenssl), you will be right back into the "mucking with the infrastructure" hell which you were trying to avoid in the first place. Except now you'll be doing it on Windows where fewer people can help you. (I do use AOLserver on Windows regularly - although not OpenACS - so I have some idea what I'm talking about here.)
Now, there is a nontrivial amount of infrastructure setup work to get the software OpenACS needs installed and working. This is true even if you are familar with Unix, but is obviously much worse if you are not.
Glenn, therefore, as others mentioned above, the fastest and easiest way for you to get up to speed is probably to use John Sequeira's VMware image with everything pre-installed. You can run that VMware image on Windows or Linux, your choice. And since everything is pre-installed, you get to focus on learning OpenACS development right off, rather than learning the annoying sysadmin side of things. (You can go back and learn that stuff later, as needed.)
In some ways, the VMware image is much better than even someone handing you an actual Linux box with everything pre-installed, because you can move the image back and forth between your Windows laptop and Linux server, if you seriously break anything you can just revert the entire image to your last saved snapshot, etc.
Another good alternative might be the Knoppix live-CD Linux images somebody made (Malte?), again with OpenACS pre-installed.
Note that I'm recommending the OpenACS VMware images or Live CDs even though I've never tried them myself. In the old aD Bootcamps, you showed up on Monday and sat down in front of an already working ACS system that someone else had installed, and I found that a good way to start learning how to actually write code with the toolkit. And being handed a virtual machine with everything you need for OpenACS pre-installed is pretty similar to that bootcamp setup.
Going with a Dev server at Acorn Hosting is also a good suggestion, as that completely elimintes the "install Linux" work, and should eliminate much (but not all) of the "install software and get stock OpenACS up and running" work as well.