I would think you have construction and use regulations in Canada similar to those here in the UK. If we produce a significantly altered vehicle from another then it may be required to undergo Single Vehicle Approval testing. This is like an extended roadworthiness test (MoT here) but covers even the smallest detail like the type of dash switches used, the bezels on the dials, the curvature of any edge or surface on the vehicle, etc. It sounds horrendous but it basically mirrors the requirements all manufacturers must adhere to in their designs. The problem for your project I would think will be the stability and weight as all thtose other factors can be worked into the design once you establish what they are.

As to insurance, the UK has specialist brokers who will insure home-built vehicles and kit-cars, sometimes on a limited mileage policy. They will require the SVA test to be complete and satisfactory and may well need other engineering detail but it should be possible - if at some cost! Examine the specialist magazines for more detail.