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If you hate backing it up enough, try a front mounted hitch...
I had a truck I used to move trash waggons around (the kind with a front steering axle and a rear fixed axle)...
Try backing one of those things up a time or two... it is the same as having a really short trailer and then a really long trailer in tandem... I don't care who you are, it is an impossible setup to back up. Turn the truck around and maneuvering the waggon was a cinch.
I had a truck I used to move trash waggons around (the kind with a front steering axle and a rear fixed axle)...
Try backing one of those things up a time or two... it is the same as having a really short trailer and then a really long trailer in tandem... I don't care who you are, it is an impossible setup to back up. Turn the truck around and maneuvering the waggon was a cinch.
That's the same setup as a 10 wheel dump and pup. Hitch is a pintle hook, long tongue and the front duels are 5th wheel mounted. When backing you turn the steering wheel the direction you want rear of the pup to go. Opposite of backing a straight trailer. After you get on to it, you can put it just about anywhere. We used to back up to a pile, dump the the pup, pull forward, jackknife the pup into a U shape and dump the truck almost on top of the pile from the pup. Does take practice though.
My tractor is a little smaller, but it fits end to end on a 12' trailer. When I carry attachments, I usually strap them to the loader or put them in the back of the truck. Kind of a pain, but it keeps me from spending $ on a new trailer that I wouldn't use very often.
In my case, the loaded rear tires are too much tongue wt to put it on backwards. As mentioned before, I pull on forward and have the bucket setting up on the front frame. This puts most of the weight on the trailer axles. Looking at your pics, it looks like maybe you should try that. Take measurements at your front wheel wells and try to get them as close to the unhitch height as possible.
I can put my 28ft camper anywhere I want but I'll be damned if every time I try to back up my lawn tractor with that 4 ft trailer behind it I jack knife it.... go figure.
When I drove tractor and trailer the longer the trailer the easier it was to back up, but as with anything else.... practice practice practice.
Now I am going to back my mower up and down the driveway untill I get it right.
Agreed on the longer trailers easier to back up. Also the wheelbase of the tow vehicle plays a part also. I used to tow my 26' TT with a 98 Expedition and could back that thing anywhere in one shot. Upgraded to my Excursion and it was WAY different, took a little practice, but I can again put the trailer anywhere I want in one try.
It's been quite a few years since I've towed anything other than my ample asset but, generally, the longer the trailer compared to the tow vehicle, the easier to back. I had a homebrew air compressor that I towed occasionally with a '63 F-300 crew cab and 6 1/2' bed. That was a stinker to back. It was easier to back the semis at work.
Also, watch your tongue weight. If it gets too light compared to the entire weight of the trailer, the trailer will start to do strange things when backing.
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