*wow* you are making a historic step! Why dont you update from FM5.5 to FM8 and then to FM15? You are going to run into a lot of problems with OS and Java updates. In your current problem I think it is related to Java
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FMS 8 was a native OSX application, not that 'java-browser-console'
Could be a problem with th OS - FMS 8 was for 10.4.x
although the java based server consoles (introduced with FMS9) really caught problems because of java updates, I would not recommend to run FMS 8 (nor the client - there are really helpfull commands after 8.5, the 'list' command came in 8.5)
I'm not a fan of latest-releases-only, but here, I would recommend a newer version. FMS14 was pretty cool, the current FMS15 is even better, but has some drawbacks when it comes to licencing (ie licence for iOS/FMGo..)