"unable to boot ios simulator" is a generic error for when the simulated runtime's bootstrap server (launchd_sim) does not respond within a certain time period. It usually responds in less than 1/100th of this time. This can occur if something is preventing launchd_sim from running. Check for crash logs in ~/Library/Logs/DiagnosticReports or /Library/Logs/DiagnosticReports
This is most often caused by the setting of DYLD_INSERT_LIBRARIES. Do you have DYLD_INSERT_LIBRARIES set? To find out, open Terminal.app and run 'echo $DYLD_INSERT_LIBRARIES'
dyld_sim will attempt to log that it is ignoring the library because it is a host dylib and not a simulator dylib. It uses logging routines provided by the host's dyld to do this, but on Mavericks, dyld has a bug and will crash. This is fixed in Yosemite's dyld.
Try unsetting DYLD_INSERT_LIBRARIES or upgrading to Yosemite if that is the case. If that is not the case, I'm curious what your crash logs reveal.