I have a similar situation as the OP. We wanted to buy a trailer or 5th wheel to camp with my son, 7 at the time, now 9. We looked at lots of travel trailers that just seemed to be built so cheap. I started looking at used 5th wheels and was surprised how much trailer you could get for the money and how much higher quality they were over travel trailers. We found a used Forest River bunk house form much less than what we saw on dealer lots. Having the bunk house is perfect. My son often brings a friend along when we camp. He has his own bedroom so the can go in there and be loud, play games or even watch TV if we have power. It's been great so far and it was priced low enough that if we didn't like it we could sell it easily. Now that he is 9 we wish we had a toy hauler, but we only have a 3/4 ton truck so we are limited in what we can pull. That's actually a good thing because it is easy to have a second house payment for your truck, trailer and toys. Our trailer is 32' and right on the edge of OK to pull with a 3/4 ton truck. It's also right on the edge of ok to get into some camping spots. I think I would only want larger if I had places I knew would be ok for the larger rigs. Most local camping areas are not or you have to be there days before anyone else or all the larger spots are taken. I would definitely suggest a bunk house as your son is only going to get larger and you want him to enjoy the trip and have his own space.