My factory remote start dies probably 20% of the time. To me it seems as if the truck stalls out. It fires up, then dies. It will not remote start again untill the truck is started with a key. If it dies and I try to remote start again the blinker lights just flash but nothing happens. I have taken mine to the dealer 3 times and they were unable to duplicate the issue and gave me a print out of how to operate the remote start (Despite the fact that the directions are on the back of the remote. Also the remote start system is a very basic thing to operate, about the same level of difficulty as adjusting the mirrors....). And no it has nothing to do with how long the button is pressed because it's done it while quickly letting go of the button and holding it in. That theory doesn't make sense because the truck is merely looking for the trigger or signal to start a process (the starting sequence).
That AC squeal thing seems unrelated to my issue but I have had that problem when starting the truck normally. It does that about every 20-50 starts.