Lancer, I was in the same boat. I essentially had no job or reserve job lined up until about 15 days prior to my actual separation date. It was a bit nerve racking but in the end it worked out and usually does for those that keep working it. Never once did I look back and say.....wow maybe I should have stayed in. Those would have been wasted brain cells and probably would have ended up giving me a set of 1 year IA orders to a not so fun place.
With the airlines not hiring I was forced a bit to go the civ sector(contractor) route and was able to negotiate the reserve gig that I was hired for. As I posted earlier, it was a very fortunate situation for me, that just took patience. That said the reserve process has been anything but easy. I'm not sure how hard the affiliation process is for the guard guys coming off AD but joining the SELRES side of the Navy has been a complete A$$ leaping event and a re-invention of the proverbial wheel for a process that is done on a daily basis across the Navy. In the end however, it's well worth the pain and the $$ is nice.