Most of my software is purchased. I do look for free first, though. There's some really tremendous stuff like TCPMP for free, as well as very reasonably priced software like DateBk5 or ShadowPlan, etc.
As far as downloads, even though I've purchased a lot of programs (on both palm and PPC, many of which I don't even use), I bet my own download

urchase ratio is probably at least about 10:1. And that's for someone who's generally really trying to buy, and who buys a lot. It's even worse if you include the programs I download multiple times for version upgrades or because I didn't keep the first copy and want to try it again after I purchased it.
I very,very, very rarely have illegal software on my pda. I can only really think of one time actually, and that was just a different version of software I had already bought. It's not worth the risk and I justify the expense to myself by reminding myself that I like to support the developers, which I do desire to do.
What frustrates me is when software turns out to be useless to me and my money is wasted. Or if the author stops supporting the software and it becomes useless. Especially if I feel I was misled or misunderstood its capabilities. Fortunately that's not too often, and the trial downloads really help. Or even when, like for Pocket Informant, I buy a copy and then 3 mos later there's a new release which I have to pay for if I want to stay current.
I'd have to say that even though developers can and do make some money and even possibly a living on development, I bet that most of them do it for love of the work and because they like offering something to the mobile computing community. I can't believe most developers are in it just for the bucks.