Do I need a WD hitch for this set up?

My thoughts are that if the trailer weights 5000lbs and you only have 550lbs on the tongue then you might want to add some weight to the tongue (think 13% -15% TW on tongue.) Only reason I say this is because a 29' trailer is a very large wind catcher and without enough weight on the ball it could start to sway out of control.

What would scare me really is that light of a trailer being so long. While you don't really need a WDH based on weights (IMO) - it might be nice to use a WDH with a sway control setup if you have one laying around.

I towed over 7,000 pounds with my classic 2007 and no WD hitch, which is about the same truck, with no problems at all. I do not recall the rating of the receiver though. That is something to check.

old guy wrote:
bout the time you get blown off the road, you will say shoulda had the WD put on

x2 - 29' is a long trailer without a WD !

bout the time you get blown off the road, you will say shoulda had the WD put on

Your hitch might be rated for only 500 pounds tongue weight without WD. If so (check the label) then technically you're over on tongue weight without it.
Either way, no, you don't need a WDH for that light weight trailer and that truck.
I would pull it without.
I tow my 4,500 boat, 5,000 pound cargo trailer, and 16,000 pound loaded equipment trailer with no WDH and have no issues at all. Yes, my hitch is rated for the tongue weight.

If you already have a WD system, put it on. Why take chances. All you need to do is slip the 2 catches over the A-frame and tighten them down. Attach the bars and you're on your way, If you're using your WD hitch to begin with.

Now, if you're using a different system, it might be more difficult.

If your's are the bolt-on type or a different system, then pay the dealer a few bucks to install them. They'll do that. I think the benefit of having them outweighs any reason not to have them, even when towing a lighter tongue weight trailer.

Now, if you have to buy new ones and you don't like what the dealer is selling, then hitch up and drive to the nearest dealer that sell what you want and have it installed.