Hey Mate,
I have an OzTent Bunker and use it for work. I spent 56 days sleeping on it last year during winter months and loved it! 1 minute to set up, 2 if you put the cover on. The cover is water proof (had to live through some rainy nights), but make sure that you tie off the end as the water will pool above your feet.
I would look into getting a mattress for the young fella, as I used a self inflating 3/4 mattress (
http://www.bcf.com.au/Product/Wanderer-Self-Inflating-Mat-Hiker/382598?menuFrom=571563) due to room constraints. If it was for 1 night every so often, don't worry with the matress.
I'm looking at getting one of those Wanderer self inflating mattresses (
http://www.bcf.com.au/Product/Wanderer-4x4-Mat-SIngle/381383?menuFrom=571563) for more comfort, but when you roll it up, the bag isn't big enough to fit it in. I have a double one that I use for the swag and draw all the air out with a 12v air pump which makes it alot smaller.
Get yourself a little pillow like the ones you can get on a plane as they fit nicely in the bag. I am looking to upgrade the bag as it is starting to show some wear and tear. I know Drifta do an alternate bag, but it will last for a few years if you don't throw it around to much.
There is pouches inside that you can put books, iPad or phones in. We use ours for the young fella when we go camping and SWMBO, Me and the Miss 5 sleep in the RV5 tent.