I do not wish to seem to be a Prophet of Doom, however, imo your course of action may not be in your best interest. In the event that not everything goes as planned down island, the trailer may have to remain there until you have completed all the necessary repairs. Have you taken into consideration that you will need to (in all likelihood ) replace/repair the trailer braking system, up to and replacement of every component with the possibility of having to install brakes on an axle that did not have them on in its original configuration. Towing a heavy boat and trailer over the Malahat (or on any road) without functioning brakes on all axles is not only illegal it is an invitation to disaster. Should you have an accident, it will be your fault, your insurance will be null and void, and any costs will come from your own resources. Should you be stopped by law enforcement, you could be heavily fined and your trailer may have remain where you are pulled over until repairs are made or arrangements for alternate means of transportation are undertaken.
The cost of renting a suitable trailer or having the boat and trailer moved on a flat deck wrecker would then seem a minor expense.
Besides once your boat and trailer is home, you will be able to work on it at your own leisure, and with your new impact as well
Ultimately though the decision remains with you.
