1. Be honest with your residents. Tell them everyone won't be able to go every time,and how important it is that they work together so that everyone get a chance to go. 
2. Have two outing a week until everyone get out at least once. 
3.Have a sign up sheet first come first serve. 
4 Let the residents selcet where they want to go the more choices you will have. 
5.Have an outing inn ex. my residents love to go eat. So what I did was gather a few menus from places that they picked. I let them vote by a raise of hands. They select. Let the residents pick what they want, follow your system for getting resident's money. Call the order in ahead of time and go pick it up.I did this and it went over very well. I hope this works 
I'v done KFC, Red Lobster and Pizza Hut.