Ok, here's the basic workflow:
1) A user inputs an order for a customer. This consists of several line items of equipment rental. (So, for example, 3 trucks at 7 am, 7:30, and 8am for June 23). (Ok, this part is easy... a standard Order resource with the usual CRUD actions)
2) A user (may be the same as #1, or may not) must fulfill the order, so he must be able to pull up a list of unassigned work (for a particular day, for example), see this work is still unassigned and assign 3 trucks to this job. (This is where things get fuzzy. Is this specialized index action on Order? I don't think so because we're editing the orders, not just listing them. Is this a separate resource?)
3) A user (may be the same, may not) must later go back and fill out the hours the trucks actually worked, so they must first be able to pull up a list of all work which has been completed to date and see this work has been assigned but not yet recorded. (Same problem... is this another resource, or another view on the resource in number 2?)