I would say a 2000 lb trailer loaded might be a bit hard to maneuver, I'm sure it would pull it flat out, but pulling while turning and on hilly terrain might pose as a bad situation, My trailer is not as heavy as what your trailer would be (Loaded),
and has no problem pulling it fully loaded, I also have a FEL that holds the front down, I usually do not pull this 13 ft trailer with the tractor but I made an exception for this event and did several pulls before I actually had people load into it, plus I pulled in low low gear,
I do have another smaller 4 x 8 trailer I pull with it for use around my property, in this picture you can see the size of trailer compared to my old kubota, the yanmar I have now is a little larger than the kubota, so the trailer doesn't overwhelm the tractor as one might would have thought,

and by the trailer being dual axles it wasn't really an issue as far as need to distributing out the weight, Oh! and I did adjust the breaks before doing this...and do have the ball connected to a Box scrap just as California mentioned, I would say no to a loaded 2000 lb 16 ft. trailer on hills, BTW I tow a trailer of some sort every day for the past 30 years, you might say one stays connected to my truck always

although of course I don't drag them through Mud in the dark
