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About the only things this old lazy fart tows any more are my two Boston Whalers, 130 Sport and 160 Dauntless, down to the Gulf. But being retired, I do it often.
Every spring I haul a John Deere Utility tractor up to maine to do food plots and also carry a honda 650 ATV in the Bed . I also tow a Utility trailer at least once a week. The truck pulls these loads like nothing 2004 F250 5.4L 4X4 3.73
I just picked up a 24 foot enclosed car hauler with 7 foot interior ceiling. It was a ton of fun towing that on I-90 south of Madison WI in a snow storm (NOT!).
29 foot Jayco 5er and 14 foot Smokercraft fishing boat. See pics in my gallery. Wish it was summer and I was pulling it right now. Instead I am looking at another 4 inches of snow falling.......
Yukon, how do you like that Jaco?? What year is it? I dang near bought what looks to be the mate to it last august but the wifey told me she was happy with what we had and being I had already bought and sold 2 campers last year she said enough is enough already, it was a smokin deal though!! Could've picked up a 99' 28ftr that was imaculate and already had the rear hitch on the camper for 8k cash, dang women just don't understand a good deal when they see one, lol!
SLE, I love it! Its a bunkhouse model which works great for my family. It's a 1999 just like the one you mentioned. If you could have got one for 8K you should have jumped at it because here in MI they are going for 10-11K right now. IMHO Jayco makes the best trailer for this price range. I've never pulled a TT and boat double like you do, but I know this setup tows like a dream. Now you got me thinking about camping...