The only problem I've had is loading the boat onto the trailer. If the ramp is steep the stern can swing and wind is your enemy also. I have a pair of rollers on each side of my trailer to help hold the hull and to center the hull onto the trailer as I pull up the ramp.
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Thats one up side to living in Australia, these types of boat (big cats) are virtually non-exsistent, so fortunately they don't have the same insurance "reputation" that they do in the US, speaking with my broker, it made not a difference between a 40ft Vee or Cat, assuming same power/value

I have alot of seat time in smaller high powered hulls, my last boat was a 21ft Deep Vee, with twin 300X Merc's that ran north of 110mph, figure if I can master that I will get there with a cat!!

I have spent a few hours in a 28 Skater O/B and absolutely loved the ride, can only imagine it improves with size.

A good trailer with tunnel guides and a good ramp, little cross current and wind and a 36' cat is not too hard by yourself. Of course a too short too steep ramp with a strong current or wind, no good dock to tie up while getting the trailer and too many people cutting you off will make it very difficult.

I have a 368 Skater, and it's easy to get it on & off the trailer, especially since the trailer has stairs between the front sponsons. You can run back & forth if you need to MUCH easier with the stairs. The biggest pain is finding a wide enough slip close by to leave the boat while your truck sits in the middle of the ramp, since it was much wider just a few minutes before! Once you're tied up, there's the problem on some Poker Run lakes dealing with getting the truck & trailer parked in a lot that was designed for Wakeboard & Bass Boats as well.

As mentioned before, tying up is no problem if you just sit in neutral and get everything ready to go before you pull up to the dock.

I have done it a few times w the TOP GUN. Not to bad when BOTH drives are working!!!

That's so sad