Should I buy a Computer Speaker or a Headphone?

I'm gonna use it for gaming and game development. I'm torn between choosing from a speaker and headphone as both of them have their ups and downs.

Speaker
1. I don't have to wear them (I wear glasses so this is really great)

Headset
1. Portable
2. Can cancel out noise
3. Can make me hear sounds when at night (since I turn off my speakers due to my roommate sleeping)
4. Can have a microphone

I currently have around $100 to spend for a headphone and I could push it to $150 for a speaker. I'm really confused as people are saying "depends on which type of sound do you like" I don't know much about audio hardware and I don't know what "specs" to look for if there are any and all those stuff about bass and whatnot.

For headphones I have my eyes on a HyperX Cloud. People are claiming that the Cloud 2s have problems and their $20 difference from Cloud 1 isn't worth it BUT my retailer is selling the Cloud 2s for $10 more compared to a Cloud 1 and I think it's a good deal since I have an integrated sound card PLUS the mic is clearly better than the Cloud 1.

For speakers I don't know yet I've read that I have to choose between a 2.0 and 2.1 which I have no idea what it's about but they say 2.1 is better but a cheap 2.1 is less effective than a good 2.0. Can anyone recommend a 2.1 Computer Speaker that's around $100-$150?