Ok here's the deal:

04 F150 Screw, 4WD w/towing package. Looking at towing a 5,000 lb tractor on an about 20 ft long deckover trailer (9999 GVW) depending on length of trailer, empty trailer weighs between 2300 and 3500 lbs (haven't bought trailer yet) What do I need for the truck in addition to the towing package:

1. Weight distributing hitch?
2. Sway bars?
3. Is the longer, heavier trailer better for weight distribution or would the lighter, shorter version be better (due to less weight) ?
4. Trailer has a 2 5/16 hitch, will this fit in standard receiver?

Thanks.

 

Questions for you...
How many times are you hauling tractor?
How far are you towing?
How about elevation and mountains...higher up you go less power.
Trailer MUST have brakes and you MUST have brake controller.

Answers
1. Kind of depends on how far you going and how often, but Yes, I would get WDH.
2. Kind of depends on how far you going and how often, but Yes, Sway bars.
3. Kind of depends on how far you going and how often, but longer trailer will be more stable as long as it and the load doesn't overload truck.
4. 2 5/16" is the ball size...receiver is still about 2" square ID. Your hitch is a little less than 2" od.

My opinion but YMMV...

 

Get a 2 5/16 ball, a tekonsha brake controller and roll.

 

[QUOTE=Shadow_Grey;4915568]Questions for you...
How many times are you hauling tractor?
How far are you towing?
How about elevation and mountains...higher up you go less power.
Trailer MUST have brakes and you MUST have brake controller.

Once a week in the summer only.
Distance of 1 hour or less (one way)
No mountains, normal terrain.

 

And a WD hitch. The factory hitch is only good to 500 tongue and 5000 gross.

 

Agree with the others...get the ball/hitch, WDH and go for it!