Enclosed Trailer - I have a toy-hauler, also use a wheel-chock in it. One chock - with carabiners and turnbuckles - and multiple uses. I do not compress the front-end when I use the chock.
Fork seals- I think there's a reason to be concerned about fork seals if you compress the front end for the ride. I don't use the chock for my dirt bike - just strap down the handle-bars. I (and others I ride with) found that seals tend to go out prematurely with that practice. Therefore, I bought a special block (with a Husky "H" on it) to put between front tire and lower triple clamp. A lot of people use these blocks when hauling dirt bikes, some even call them seal savers.
Bottom line - it's a good idea to haul your bike if circumstances make riding it impossible or inconvenient. Take a bike with you whenever you can. It makes every trip more fun.