My Trailer Aid also did not work on my Weekend Warrior without adding blocks or boards under it first. On my current Interstate trailer, it works as designed so you have to look at how much suspension travel you have or how heavily you are loaded to see if this is an easier method compared than jacking it up. I like the hybrid method of driving up on a ramp and jacking up the axle on the flattened tire if it doesn't clear.
I would also raise the tongue jack to where the tow vehicle was at unloaded height which would give me a little more clearance on the front axle or drop the WDH bars so the rear axle would get a little more height.