Hi Bill, I've reading about your trails with Monticello/Metacello and been surprised about all the difficulties you are having. I frequently load fairly complex configurations on top of Pharo 1.3 without a problem.
You can flush Monticello caches with: MCMethodDefinition cachedDefinitions removeAll. MCFileBasedRepository allSubInstancesDo: [:ea | ea flushCache]. and try removing the 'package-cache' folder from the folder containing your image. other than that, as others have said if you can isolate the problem we stand a chance of helping you Nick