Not stupid questions but questions that can be complex and expensive to answer.
Here is a link to an organization that has been set up for answering questions such as these. I have no idea if there is a local chapter in your area:
You give no indication of how much expense you can accommodate and how much assistance you have available for doing the building so the following may be totally impractical.
My first thought about what you want to do is that you should try and get an old power wheelchair; obviously you travel the route your 'Transport Module' will travel so a wheelchair can do it.
For many years now power chairs have had tilt and recline seating systems which are operated by linear actuators so this is the type you need; you don't actually need the seat system but you want the actuators and the joystick control module that can switch between driving the chair and adjusting the seat.
Strip everything off the wheelchair so you just have the base with wheels, motors, batteries and controller and build a hoist or maybe some kind of forklift arrangement in place of the seat; use the actuators to move this. Wire the actuators into the control and lengthen the wire between the joystick and the wheelchair so you can drive the Transport Module from your chair.
The forklift arrangement I am thinking about is like the ones you see at The Home Depot where the forks extend forward from the drive base.
Technically I think this would all be fairly straightforward; cost ?????