Lots of variables here......not "bashing" any one's Jeep, but there are a few things to bear in mind. When Jeep went from the "TJ" old body style to the "JK" it helped but the motor and transmission wasn't as robust as what was in the "old TJ". (TJs were built from '98 to '06) (JK's are from '07 to present) However, Jeep made a very strong attempt to "fix" these problems. In '12 they went to a New Pentastar motor. It has 285 HP. The "earlier" JKs had about 215HP, and the TJs had about 170HP.
The advantage of the TJ is that the motor and tranny are tried and true. The I6 4.0 liter has been around/ used since the mid '50s. It is strong motor and known to go well past 200K miles. The disadvantage are also its age. MPG not as good and power is "down" compared to most vehicles. A TJ will get you there but it will take its time doing it.....lets face it Jeeps are not race cars.
A TJ would easily be able to pull a lightly loaded landscape trailer. On a daily basis I wouldn't want to be much over 1500lbs. However it would also need about 3-4 inches of lift to fit 33's.
A JK is rated to tow more than a TJ and would "fit" 33"s almost stock. a leveling kit or spacers/ different wheels would probably fix any issues. The disadvantage IMO I wouldn't get a JK unless it is a '12 or newer...and for what they ask for a '12 you may as well go new....which would almost push me back to the TJ...if I didn't want to spend the coin for new.
I realize this probably just made it "harder" to choose, but the thing about Jeeps...you have to choose what is right for you. For light off roading and towing like you are speaking off, I wouldn't hesitate to go newer and try and write as much as I could off as a business expense...including the winch for pulling shrubs.

GOOD LUCK!!