I made this guide especially for newbies and those looking for role-playing as a street-gangster. To the people reading this with sufficient experience, I hope I can help you with at least something to improve your character development a bit.
Now, we all know what it is, and for the most people, it sounds noobish. Actually, roleplaying a street-gangster is one of the most funniest character roles you can portray. To start with, gangsters are not involved in crimes every single time. Just normal people, like you and me. They are not always on the negative side, like they go out and eat, hang out with their friends, play video games, have hobbies. This is very important, that you should become friends with other people and develop relationships with them just as you would in real life is also a thing. You should frequently do things with them separately rather than hang out in a group.
Main goal of a street-gangster is to be a part of a gang he wants to represent. It's UNREALISTIC to join a gang by approaching them and saying "I want to represent", or "I saw y'all hangin' around". There's a lot of examples compared to that, still, try to develop your character realistically into a gang member, you should roleplay that you are from a neighborhood where the gang resides that you want to join so you can be dragged along to the street life. The gang members don't want you to join by saying that you want to be involved in their illegal activities. Just to state, DO NOT ROLEPLAY A 25 YEAR OLD+. Join the gang by starting off at an young age, because in real life gang members don't survive their twenties. They either end up killed or locked-up in prison, or they might end up as shotcallers and veterans. It does take a lot of time to fully develop your character at that age, but it is honestly worth it.
Hang around the hood, SETTLE UP SEVERAL RP SCENARIOS. Don't hang around by doing /rap 1 or driving around in a car for no reason 24/7 listening to custom musics. Most of the gangs look for you to show character development, otherwise you will never be initiated into the gang. Don't mess with the members in the gang, as you need to show respect. By that, I'm not saying roleplay a fainthearted guy, but you'll have to keep it in mind that you're a nobody towards the gang and it's members self.
In the hood, there will be a group of ragged(loyal) members around having it about their business. I suggest to let them do their talking, and find other people such as outsiders around the hood to start your own conversation. Can't you find others? Go and put in some work by spraying graffiti around the hood.. not your thing? Roleplay walking your dog out, go gamble with other people, etc. Other than that, you will most likely notice other outsiders hanging around the hood, doing nothing. CHANGE THAT! OG's or ragged members will notice the creation of your roleplay and appreciate that.
Eventually, you'll be slowly introduced into the gang. However, that's the thing where your relationship matters with the ragged members. If you've earned their trust, and if they think you're capable enough, they will be on your sight and recommend you to the OG's to get jumped in. If you cause beef, and stand around doing nothing as I stated before, you will NOT get induced into the gang. At this time, you know what's up with the gang. You know to throw up the signs of the set even though you're not affiliated with it YET.
To proceed into the gang, you create roleplay to get noticed easily. Don't just say "Word", "Aight", "True" to the ones that are trying to start a conversation with you. Another way to get noticed? Sure. Start a roleplay log for your own character with a clearly defined background/story and post roleplay screenshots in there. You'll not be noticed by the ragged members only, but straight up other people that will give you tips and other stuff so you can improve the development of your character. Of course, there will be people who don't respect your roleplay and reply with negative comments under your log, as if they were the best. You need to ignore those and continue building your way up with your character. You might be like, "This is nothing for me, starting a roleplay log". The gang has a thread in the section (CLICK ON IT) "Organizations of Los Santos", you can also post your roleplay screenshots there under the corresponding gang thread to get immediately noticed by members of the gang self. Also don't let a specific roleplay/gang define your character. Everyone has some type of personality. Roleplay a character with personality inside AND outside the gang.
I'll keep this thread under heavy construction.