Not a 2nd gen, but have use my v6 3rd gen tacoma to pull my boat/w trailer thats gotta be at least 3k lbs. to different local lakes here. The truck has towed it without any issues not trying to push it over 60 mph on these secondary highways, and back roads. I definitely wouldn't attempt this with a 2.7 engine...they already have a problem feeling underpowered when totally empty, and with nothing in tow.
I've also got a 5x10 aluma utility trailer I use to tow my 500 lb + snowmobile up north. Most of time you can't tell its there.
