I guess I should have mentioned the $300. The way I look at it, you have 30 days to see if OpenACS is for you. From day 1, you should be able to write code and see if Tcl/ADP/etc agrees with you, and if the modules actually do what you want or can be tweaked to do it easily.
If they do, in 30 days you get to make another decision: is it worth $300 to not allocate a new hard drive/partition/box and set up Linux/Pg/OpenACS on it? For those of you with (lots of?) time or interest in learning how to set up software, go the do-it-yourself route. For people who'd rather dive right in and code, and forego all that wonderful sys-admin and hardware-compatibility knowledge, pay the VMWare people for taking that task away.
I think the no-cost-for-30-days try-it-and-see approach benefits people in both categories.
I think that a Windows-installer type of thing is a good idea, but realistically OpenACS is going to be a second-class experience on that platform for a long time, esp. given the AOLServer development roadmap.