I looked at the Rotorway before I bought my R22. I flew one for an hour and was actually very inpressed with it. It was a lot cheaper, but it is generally said that you have to do around 2 hours maintenance for every hour you fly it. As I wanted something to fly rather than tinker with all the time, that was a major reason to go for the R22 instead. I do have a kit fixed wing plane that I maintain myself, but there are rather less moving parts and things to go wrong than there would be with a helicopter. Also, I wanted to share the operating costs with another pilot, and there are very few Rotorway rated pilots around (or even those who will fly in one), so my potential market was that much smaller. The R22 despite its detractors is a well proven and reliable design, and as such has an excellent resale market. The only snag is the time/hours life that really hits you with the depreciation. There are always several Rotorways available for sale so the resale market is that much thinner.
Having said all that, I am delighted with my R22 and would not swap it for anything other than maybe an R44, but I don't need the extra passenger capacity so I doubt if I ever will.