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FIRST BIKE FOR A 56Y.O./250lb nOOB

One thing you can do to make a hitch hauler more stable is to add straps going from the ends of the rack to the stake pockets above. This is a really simple solution for open bed pickups, and keeps the whole rack from shifting back and forth. Those hard oscillations is what can cause the main hitch to break.

No trailer this time?
In California, bringing a trailer means 55 mph speed limit. I was able to put the pedal to the metal with this setup last weekend. This bike was only 200 lbs, so little worry of breaking anything.

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A keen eyed viewer will notice I upgraded the Versahaul to a sweet length of 2 1/2" x 2 1/2" x 1/4" walled tubing for the center bar.

Also made 2 1/2" anti rattle clamp. similar to this style, but beefier

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With the 450 on there is does not move.

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I'll second the notion of putting the greater share of your investment into high quality gear, and the lesser share into a less expensive older bike, but avoid project bikes. Needs tires & chain is ok, needs carb cleaning too...walk away. You want a bike that is being ridden, not 'ran when parked'.
 
All good advice above, a KLR would more closely resemble your dream of a GS and be a decent starter bike with good low end power. They don't crash as well as say a DR or DRZ. But with crash bars and good handguards they usually fair pretty well in a tip over. Also the cockpit is a bit better suited to a full size rider. Personally I chose the DR and my son's ride DRZs. All great bikes, but we err more to the rougher end of dual sport and they serve us well. Do you have someone to ride with? A real good idea when you're just getting started and it usually adds up to more fun as well. A rider training course will benefit you greatly as well and is always worth the time it takes.
 
DRZ400 or a new KLX300 are both dirt capable bikes.

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I absolutely agree!

My story:
I had a couple of sport bikes several decades ago but never really knew how to ride. Last year my kid talked me into getting a bike and letting him get a dirt bike. I wanted something I could use more than just up north so a dual sport was the obvious choice. I narrowed my choices to the CRF300L, KLX300 and DRZ400. I wound up with the KLX and I absolutely love it! It's been a great bike to learn the finer points of riding.
 
My suggestion would be a DRZ400S. I picked one up to start dirt riding again at 65. I weigh 260 lbs. I bought the correct Racetech spring for my weight and really enjoy the bike. It is fun to ride around the back roads as I live in the country. The bike has gobs of torque and will run 60 mph comfortably. It weighs 317lbs and I find it easy to handle. It is a simple, rock solid dual sport that can take you through any terrain you have the skill for. A smaller 250 may be better for initial learning, but you will quickly discover it's lack of torque and HP with your weight. I would pull a small trailer rather than loading and unloading on a rack hanging off the back. They have been making DRZ's since 2001 with virtually no changes for a reason. They just work, and keep on running.
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My suggestion would be a DRZ400S. I picked one up to start dirt riding again at 65. I weigh 260 lbs. I bought the correct Racetech spring for my weight and really enjoy the bike. It is fun to ride around the back roads as I live in the country. The bike has gobs of torque and will run 60 mph comfortably. It weighs 317lbs and I find it easy to handle. It is a simple, rock solid dual sport that can take you through any terrain you have the skill for. A smaller 250 may be better for initial learning, but you will quickly discover it's lack of torque and HP with your weight. I would pull a small trailer rather than loading and unloading on a rack hanging off the back. They have been making DRZ's since 2001 with virtually no changes for a reason. They just work, and keep on running.
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That's an awesome bike and sound advice.
 
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OP, any update on a choice yet?

FWIW, I started riding a year-and-a-half ago at age 53 on a tw200. I weigh close to 300 lb fully geared and rode it stock with no problems. I had a hitch rack on the back of a small camper trailer, and loading was not a problem with a 4-foot ramp.

I have since moved up to a Honda cb500x since I ended up doing more on road riding than I initially predicted.
 
The bike would at least be a 2nd mode of transportation and carried by 1ton+ 4X4 truck camper.
I camp in the back country and would like a snoopNpoop and a backup means of travel, hence, the on/off road capability.

I don't see me doing more than 45MPH~.

Depending on how far in the backcountry I am at a given campsite; going into town for stuff or following a trail that's next to said campsite via a maintained/unmaintained fire road would be the INITIAL main purpose.

Three things can happen:
1) I'm satisfied the beginner-motorbike serves it's purpose as described above/not interested in upgrading bike.
2) I'm digging the bike enough to want to upgrade to a more-capable bike.
3) I don't like using a motor bike as described above; will sell bike.

If you can find one a TW200 might be the perfect bike for you. Its basically a 2 wheeled tractor and super forgiving for a beginner to learn on. Super good for just poking around and taking in the scenery which is what it wounds like you want to do. With added racks and stuff they become like a pack mule too.
 
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