Rudy & The Dilema

I am allergic to this sweet, cuddly kitty...I love him though. Lily and I got him from the Waveland animal shelter in March. I have a guy named Dennis that will take him, but Rudy will have to live outside...which raises some questions: what if he get run over? Where will he sleep? Will the other cats Dennis has like Rudy? What if something happens to him? I feel like I made a commitment to Rudy when we adopted him, and now I'm letting him down. I've also thought about asking Ben to take him...then he could live in the house, and sleep in the bed (like he likes to do). I love Rudy-Tudy.....and I don't know what do to. I'm very sad (although I suspect Rudy will be glad to get away - FAR away - from Lily).