Not very outstanding at all. I bought it last year and have used it a total of zero times (whose fault is that, mine, correct, but still, it stings that they have a shitty upgrade policy).
Well $99 for a developer tool is quite some impulse purchase. Can I gently suggest that your upset might be more a case of buyer's remorse than dissatisfaction with their upgrade policy?
If it helps, it does come up on things like MacHeist occasionally, and they have sales once in a while (there's one now, at $79.99, but I've seen it as low as $50).
Try and contact the authors, it's likely that they will give you at least a better upgrade price for version 2. Some companies also give out upgrades like that for free for people who bought previous version just before the launch.
It's on the Mac App Store, which doesn't permit this kind of thing.
It's not so bad: I'll try the free trial and if it fixes some of the problems I have with PaintCode 1, I'll pay for the upgrade. The app itself is a tool which helps me make money so it's not hard to justify.
I'm starting to think that an honorable and smart thing for developers to do is to run a sale a month or so before the release of a new paid version on the app store.
That would be approximately why I was able to get PaintCode v1 in a MacHeist bundle super cheap in January. Very worth it - if you're going to embrace the UI dynamics in iOS 7 and beyond, this is an incredibly efficient way to do it. An update of our cooking thermometer's app (http://supermechanical.com/range/app if you're curious) that's in review now will have a circular cooking timer widget - drag in a circle, see the wedge of a clock face you're selecting - and with PaintCode I just drew a wedge and designated the angle as a variable. Didn't have to think one bit about drawing arcs, and even better, it took away much of the penalty of tinkering with the look and feel of the interaction.