So I'm going to try and get into skating, I'm even getting a longboard tomorrow before moving on, and am listening to music I used to listen to in high school and middle school because I want to feel young again.
What are some good games?
I got a PC, PS2/PS1, PS3, Xbox 360, DS, and 3DS Vita and PS4 but I don't think we got any skating games.

I enjoyed THPS 2 & 3 so I'm going to picking those up, I gave THUG a try recently and had a lot of trouble. I found that it was really difficult to tricks. Is THUG 2 an improvemt when it comes to my issue? Also I heard the Skate games are good, what's the best one and do they have a story mode?

Doesn't have to be about skateboarding, but sports is a bit broad

Paperboy
Bad n Rad Skate or Die (make sure it's the gameboy version, not the NES one)

I have never liked any more modern ones. As well as Skate, there is also the Tony Hawkes series.

The Skate series are the most fun imo and also the most in-depth skating games. it's on xbox 360/ps3 and is Backwards compatible on xbox one.

It has a single player story and everything.

The Skate series is unbelievably fun and the big series I'd recommend. It does have a story mode but back in the day, I just enjoyed skating online with friends. I know that Skate 3 is B/C but I'm not sure the online numbers these days.

Thps2