Kenny,
Debarking gets harder not easier with time in my experience with osage. The main thing that is easier is the sapwood is easier for the knife to cut through when its still got moisture in it. Once it hardens its more work, plus you want to make sure you do'nt leave the bark on so that if there are bugs in the bark that they cannot do any damage to the rest of the stave. There is nothing easiy about debarking one way or the other however keep your drawknife plenty sharp and it will make it less of a struggle. I don't know about the cherry as the only thing I have workied with there is cherry boards. Do not paint the belly. The moisture has to have some where to go and its through the belly that you want to force it to escape to prevent checking. If you ever get the chance to read Dean Torges book " Hunting the Osage bow" he does a nice job of step by step telling you how to select, cut, and process your staves. Once you have done a couple loads you will be a lot smarter on how you do what you do. I don't think you can get the twist out that way in green stave form, you might be able to rough it into roughly bow shap and get a lot of the wood off of it and then steam and clamp to correct some of it but if its not too bad then I would'nt worry about it. I don't know that this a rule of thumb but I heard someone on here a lot more experienced than me say they don't like twist over 40 degrees. I suppose that tells me that if they can work a stave up to that much twist then you probabley can too. Hope that helps, Danny