You should fit in well, sounds like you ride like most of us more mature riders! I don't have much to offer on 250cc bikes as I have no experience with them as adventure bikes but would be concerned with their lack of speed and comfort for longer rides, something to consider would be whether or not a rear hub cush drive is fitted, they make a huge difference to rideability.
DT230 or WR 250 are the only two I can think off that suit adventure riding (wait for more expert opinion on those, I've only trail ridden the WR).
If you want off road, look on Silver Bullet web site and do the farm rides, Rodney club has a clay based track at Dome Valley, don't ride Riverhead unless you wish to experience frustration but the Waitemata club will be starting it's Woodhill (Muriwai end) trail rides shortly and they are great fun, not as sandy as The Sandpit.
If you can perserve with The Sandpit you will become a good rider, once you learn to carry some speed the sand is far less problematic and it's a skill that transfers to most other surfaces.
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