AndyDRHuddleston,
You can obtain the permits through the use of any of the agencies listed above and it will normally not be a problem (FYI: Pretty much all the companies listed go through United in Damascus to obtaijn permits for the region). However, sometimes they actually deny your application for whatever reason they believe is justified that day. I have never been able to figure out why and it has happened with different agencies trying to get it at different times (i.e. not for the same flight).
You ask about weekends...remember that the weekend down there is not Saturday - Sunday but Thursday - Friday (Please correct me if I'm wrong). You should still be able to get a permit, especially if you give proper notice...
In Kuwait you would be best off using Kuwait Airways for your handling (actually believe that's the only choice
). They are not the best in the world but the do try really, really hard and are generally very nice to deal with. They won't help you with weather and flight plans though if you're a private flight. You'll have to talk directly to the local CAA guys about that unless your flight support company provides you with all this.
Best of luck!
Will
