How long is your trailer, Maverick? Single, or double axle? Where the tractor is secured should balance the load over the trailer axle(s) with about 150-200 pounds of tongue weight.
I frequently haul my X748 from my house to my Mom's, about 20 miles each way. Sometimes I'll have the loader and something on back as ballast (usually my tiller or box blade), sometimes the PowerFlow and MC519. On occasion, I've hauled the X748 and my GT235 together. They pretty much fill up my 14' tandem trailer.
With loader and tiller installed, I can back the tractor on until the tiller is against the front end of the trailer. I drop the tiller, and dump the bucket so the lip is against the trailer deck and starting to lift the front tires. I strap it down by the 3-point arms with ratchet straps pulled toward the trailer front. The bucket keeps the tractor from shifting, I rarely strap the front down with the loader in place. The tractor's weight balance is perfect in this position.
If I only have the tractor and mower, I center it over the front trailer axle, lock the brakes, drop the mower deck, and strap the rear at the bottom of the frame near where the 3-point arms attach, and use straps from the loader's crossbar (permanently attached to the tractor) to secure the other end. I always back my tractor on the trailer, and drive straight off.
If I haul both machines, I back the X748 on first, then drive the GT235 on forwards, and tie their bumpers together (the plastic cover on my GT235 is long gone), then strap the X7 at its rear, and the GT235 at its front.
Never lost anything overboard.