A TM sounds great for you! I would get the PU, they just ride a lot better with a bit of a load and you can carry a lot more stuff. As far as model, just select one you like (a two bed model is a must with larger kids). All models have higher that average resale value. The 2720s and 3023s seem to sell the fastest.
As far as towing, you could not make a better choice than the TM to learn on. It is very easy and presents almost no problems. You do have to watch the weight. Keep a good eye on tires, but this is true with all trailers.
Wishing you well.
Windy
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