Morriski_Check out skateboarding made simple volume 1 by Aaron Kyro, it teaches you step by step how to work up from an ollie to a kickflip/heelflip and everything inbetween and goes through each step really thoroughly, it really helped me
Those videos are helpful, but that dude is such a weenie lol.
I like my setup to be a skateboard setup that can also act as a cruiser. So basically I ride a wider(8.5"+), usually funky shaped deck (more fun to ride), independent trucks, and some softer and larger Bones wheels(not longboard wheels, but like 54mm). It creates a pretty surfy fun board to ride. And since it has softer wheels it rides much smoother, like a cruiser. IMO it's the most fun way to skateboard, and it's WAY more fun than a basic setup, but its definitely not the cheapest way to skate. I think a whole setup like that is probably around $175, but buying a decent complete is at least $100+. Make sure to get good trucks though. Cheap trucks will be dead in like a year, but some good trucks will last years.