Unique Issue - Best Solution for a step by step process to update a record?

Unique Issue - Best Solution for a step by step process to update a record?

I have a unique client doing rentals. They have a 'check in' and 'check out' process. Basically based on the information in a custom module, determines what items get prepared for this person's order. There are a lot of conditional statements to show/hide fields and even require certain ones. There seems to be various ways to accomplish this and all have their pros/cons. I've dabbled in workflows, zoho forms, and even creator. I'm really looking for the easiest and fastest path to a solution. They have major issues with missing things during check-out because the record is overwhelming to the people preparing orders. Must be simplified and step by step.