I'd love to hear some take-out tips from those in the know.
Being lazy and impatient, I'm always looking for a shortcut. Also, I don't like scratching on the boat either, so after loading, I wheel it right into the water, stern first, to where the bow floats. After all gear is secured, Drive is installed, etc, I tilt the boat slightly and extract the wheels from underneath, stow the cart aboard and leave -- one trip.
Coming out, the procedure is reversed. With all gear secured, I tilt the boat slightly, feel for the groove, then scupper, slide the cart in, remove the Drive and roll the boat (with gear) out of the water up to the parking area.
With the PA, inserting the cart from underneath takes a little practice, but there isn't any Hobie that won't work this way, including the TI with outriggers.
I use the light duty cart. Four years old, it has handles all the boats including the 190 lb. TI on all surfaces except soft sand. It has low buoyancy, so is easy to control under water. Any of the air filled wheels can be difficult to insert unless you replace some of the air with water (or anti-freeze mix if appropriate). This makes the cart heavier, but manageable when positioning it under the boat.
You have to be willing to wade up to your knees and get your arm wet up to your elbow to do this, so in colder water it may not be feasible.
For those who find it necessary to roll the boat on its side for cart insertion, a short-nap carpet sample is a great asset and easily stored. You can get them at any carpet store for about $1; it will protect your boat on any terrain. If it gets muddy or sandy, a quick rinse in the water will clean it right off.