Creating Non-Standard PDF Form (InDesign?)

I've been tasked with creating a PDF form to capture the addition of components to our network. It has been some time since I've made a form beyond a few fairly basic fields, so I wanted to confirm the following is reasonably possible via PDF, and if I should approach this via Acrobat or another program (e.g., InDesign).

• A set table format that expands depending on how many assests need added
• Have the ability to upload attachments of images or similar artifacts describing what needs to be added to the network diagram
• Ability to attach a non-standard/unfamiliar file format
• Several boxes for signature as document gets approved at certain spots in the process