Reddit mentions of Tcisa Tire Inflator

Yes to both questions.

First thing you need to do is fill that pack up. Should have a tire plug kit, a small compressor (I recommend this style: https://www.amazon.com/gp/aw/d/B071R5FQG4/ref=mp_s_a_1_4?ie=UTF8&qid=1523532200&sr=8-4&pi=AC_SX236_SY340_FMwebp_QL65&keywords=air+compressor+tire+inflator&dpPl=1&dpID=51KVThD3psL&ref=plSrch they last a lot longer than the cheaper, diaphragm style ones. They are also much faster. That's not the specific model I have, but close and I've had it for 4 years now whereas I would go through one of the cheaper ones every year or 2. I carry tire slime as well but hate using it because I mount my own tires and that shit makes a mess.

Also, carry a ratchet strap long enough to go around one of your wheels. It's the best way to get a tire back on the bead of you break it off on the trail.

First aid kit.

Tow strap. You should never use your winch as a tow strap. It's for getting you unstuck, not other people. If you have to use it for other people, park your atv around a tree or anchor your atv to a tree with the tow strap and pull them out with the winch power, not engine power.

I'm sure others will chime in and if I think of anything else I'll add it, but that should get you started pretty well. I highly recommend helmets. Especially if you're riding with your kid, since it will set a good example and hopefully encourage continued helmet usage. I know mines saved by noggin. I'm the only one in my riding group who always wears a helmet, but I still do it.