Coolant is a easy check. Just pop the hood and look.
Oil... that's trickier. You want the engine cool, otherwise the oil will burn you when you touch it. You also should park at a flat spot before checking.
I check as often as I can, but its maybe once a month for oil. Usually once a week for a few weeks after an oil change, to make sure that nothing is leaking.
For inflating, one of these is small, really simple and works just fine:
https://www.amazon.com/Ryobi-P737-18-Volt-Inflator-Included/...