My Deere skidsteer (70hp) with cab and 6 weights weighs near 10k lbs. My 24' bumper pull equipment hauler (6" channel iron) weighs 4k lbs. My 25' gooseneck (made of 12" I-beam) weighs 5900 lbs.

With the skidsteer on the 24' bumper pull trailer I need to put 25 lbs in my air bags to level it. With the gooseneck I can get by with 15 lbs.
Even though the skidsteer and bumper pull trailer weigh less I much prefer the gooseneck hitch as it puts more load toward the front of the truck.

I would get max tow for sure unless you are talking about a 5 mile drive once or twice a year and you are talking about a very small skidsteer and light weight trailer. Also expect the rear of your truck to be quite low if you go bumper pull with just the "regular tow" package

I tow nearly every week and have airbags and the engine tuned and wouldn't be without either.