Being a one man operation and doing the whole entire thing, and also having a full time day job, I don't have much time to allocate, and have to account for every hour. The time invested in making a Windows version of a program is small in MetaCard or Revolution, but the marketing isn't. That's what takes the serious time. I think my game plan is to be OS X only, and maybe support Classic too, and see how that goes. If I'm doing well, I may take whatever is selling best and create a Windows version.
I understand. For myself, I'm planning to do both Mac and Windows. That way, even if I don't have time or money for the best Windows marketing, I think the sales will still be higher, and I can promote with confidence that almost any home or school could be a customer. That means you can also promote in places which wouldn't have otherwise been feasible. Also the knowledge that there won't be any barriers to word-of-mouth from customers to people they know, etc.
3. Consumer apathy about paying for shareware. Seriously, there's still plenty of people who are wondering where Napster went because they don't understand why it was ILLEGAL.
Something that can be done here (I think) is considering carefully what to offer before and after registration. The things I sold best had more limitations and offered more afterwards--a reading software that only had three demo texts, but after that you could use any file, and a math game that only let you do multiplication with 1 thru 6, afterwards any range and operation(s).
My best-looking game only let you play one difficulty level and one of three areas of the subject matter (points, slopes, angles), but as points was probably the most desired area anyway, I think it ended up that they could play basically all most people needed in the demo. Very few registrations.
(So I guess actually OSX gives us a chance to correct past mistakes :-)
For some considerations about that, try the articles and forums here (I found them courtesy of Ken Ray's page):
http://www.dexterity.com/articles/
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