Point taken about the trailer. Unfortunately I don't think that my 06 tacoma has the ideal power for towing a trailer. I'm not really a fan of large trucks either.
As a side note I towed the jeep around town (20 miles or so) in 2H with no reprecussions....
Around town is one thing, on the freeway, downhill and actually needing to stop at 60mph is another. Depending on your Jeep it is between 3,000 and 4,000 lbs, check what your Tacoma is rated for. Yeah it is embarrassing to be the slow poke up hills if you don't have enough engine, but it is not embarrassing (For Long ) without enough brakes.
Think about it and verify, when you need it, if it is not there ,you won't get a second chance.
__________________
Scott
1985 CJ7 T.H.O.R
"He brought me up out of the pit of destruction, out of the miry clay, And He set my feet upon a rock making my footsteps firm."
-Psalm 40:2
Yeah the tacoma can pull a trailer of that weight [aprx 3500 lbs]. Standard towing capacit on the tacoma is 3500 and max towing capacity is 6500[tranny cooling?]. Now having a trailer + the jeep might be too much. I don't have space for storing a trailer right now anyway.
Also while the weight is within the range of the tacoma- it probably doesn't pull it well compared to other vehicles...
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) without enough brakes. 
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