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I have had this problem and can and can't help. Firslty, I have my own personnal site hosted by a web hosting company (Lost-Doggies UK) and I host an XOOPS site on our server at work for my team using Windows Server 2003, IIS6 etc.
NewBB2 on my personnal site did not detect either ImageMagick or NetPBM at first despite being told to auto-detect, but NewBB still worked OK. So I just left it. After about 3 weeks, odly enough, NewBB then showed that it had detected the imageing programs. Not sure why it took so long, but it did eventually auto-detect them. I also asked my host company what the path of these programs are, and I was told by them that there is no path as such, and it is just detcted by the server? I took there word for it, until...
In the case of my work Intranet site - I've installed ImageMagick but cannot work out how to tell any module (MyAlbum and NewBB2 included) what the actual path to ImageMagick is. I know that it is on the server under c:\program files\imagemagick, but you can't tell XOOPS modules a path like that (well I can't anyway). I tried it, and it didn't work. If you use Linux, you can give it the /usr/.../ paths OK apparently.
I've asked the question on Peak.ne.jp/xoops and was advised to try out NetPBM instead. I never have found out how you give an XOOPS module a windows server path. I've asked that question here at XOOPS somewhere but I don't think it was ever answered.