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To begin, a four-stroke (4t) actually require a bit more maintenance than a two-stroke (2t), so you are going to spend a bit more money there if you go the route of an MX style bike. Trail bikes such as a CRF230F or TTR230 tend to require less in terms of engine rebuilds over teh other bikes, but they still require a fair amount of maintenance. Bikes such as the WR250F or CRF250X will require a little more attention in rebuilds over the 230s I mentioned, and the full on MX bikes like a YZ250F or KX250F will require a good deal of rebuild time in comparison. If you are on a budget and want quicker fixes that are relatively cheaper, go 2t and be done with it.As for what to start out on, from the sounds of it you again need to go the route of a 2t, say a 125 to 250 for your height and that you have experience on a bike. A bike is a bike, it just depends on where you ride it. There are little opportunities to jump a tabletop or a log on the street, but the power delivery and torque are comparable in the same engine size range. You also sound as if you are going to hit up trails, so again i would go with a 125 or 250 2t bike. However, if you are going to hit up some serious hills, and weight over 150, you might consider the 250 over the 125.
As for your wife, I agin would say that you need to stay in the 2t range of bikes if you are on a budget. I would not go any higher than the 100-105c range though due to her height, and I am assuming she is fairly small in weight as well. Maybe an 85cc 2t bike would work better. They are smaller in height (the 85-1-5cc range) and weight less than other bikes as well, plus they are not a full size frame like the 125 or 250.
Now, if you are not on a budget, then you have no worries and can go with a 250F, a 125LE for your wife, or even a 450F for you and a CRF230F/TTR230 for your wife. I will say that the 230s are generally cheaper by a few grand as well.
Give us some more info on what you are used to riding on the street and where you plan to ride and the terrain and we can help you better. I am long winded, but all of that is a simple overview really. Hahaha!
Your son should be able to ride a Honda CRF80 or Yamaha TTR90, that are about as quiet as a sewing machine.
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