I have a 32-inch Torklift Supertruss Extension with SuperHitch on 2015 Sierra 3500 SB - Single axle. 2500# Northern Lite TC in the bed pulling a 4500# Barefoot Nautique.
Few Comments:
1) The difference between the stock hitch and a Superhitch is night and day. There is no movement of the Supertruss and the trailer is rock solid at all times. (no weight distribution hitch)
2) Double check your tongue weight - the rule of thumb is 10% trailer weight if loaded properly.
3) Look up hitch extension carrying capacities online. You will see that increasing length DRASTICALLY decreases load carrying on a single receiver hitch.
4) There is a SIGNIFICANT cost but you said "want to feel and be safe when towing" - The Superhitch and Supertruss are the tickets.
5) It is fine backing a trailer with an extension. I launch and retrieve my Nautique on about any boat ramp. If there is light, I can get there (even without light at times).
If you are going to traveling all over, don't fret about your hitch. You'll have trailer tires and hubs, low bridges, closed campgrounds, fuel stops and more to think about. Don't max out the hitch - it will keep you and your fellow motorists safer.