Well the resale argument doesn't really apply to a hackintosh - I wouldn't need to sell it - not at least in 5 years or so - I can just keep upgrading. And a 5 yr old iMac will fetch you roughly $200 from Gazelle.
About time - I suspect more than a handful of people will find spending a day here and there worthwhile if it saves them $400 + $169. (Also if in best case Apple keeps your iMac for 2-3 days in repair - that's time lost as well. You could do the Hackintosh repair faster yourself.)
The OS upgrades however - yeah they will be a pain. I can see that as a significant deterrent.
