Thanks very much for the response.  I was able to setup a Order Guide for this that kicks off the different catalog items - its incredibly close to what I am after.  I am wondering though, how would I ultimately change the Short Description of the Request, RITM and SCTASKs that are generated to show the name of the person that's being offboarded? 

I've set up 3 variables on the Order Guide, one being the offboarding users name.  I was hoping to have that variable cascade through each RITM and SCTASK somewhere in the Short Description of each, if possible.  Is this possible?  

As you can see, it does kick off all RITMs and Tasks under one Request which is super awesome, just need to get the Short Descriptions to include the name of the "Person leaving" and End Date as well.