Update: Added in the gameplay section. The next update will be a big one, and will add more content to the characters and gangs sections, as well as location description.
Your gameplay update was a big one from where I'm standing! You've added a ton of cool sh*t. The drugs, prostitution, kidnapping, extortion. Warehouse robberies... I could go on. This is great.
I like the drug, prostitution and kidnapping features a lot. You haven't evolved the core mechanics of the first two much (more extended them) but these ideas are quality:
Players may also purchase properties that can be turned into drug labs and drug dens. At first they will be undefended and only make a small amount of profit, however as time goes on the they will make much more money, drug labs will produce more product to be sold onto the streets via dealers they can hire, and the player can hire protection. Occasionally, one of the player's dealers might keep revenue for themselves and require a good intimidation.
there is now Lab Crashing and Lab Defense. Lab Crashing is where players are tasked to destroy a gang's drug lab, while Lab Defense is where the player must defend their own drug labs.
Eventually, as the player gains more revenue from their brothels, they have the option to hire goons to protect their brothels and will have the option to send prostitutes onto the streets for additional revenue. Now of course, the more money the player makes, the more attention they'll receive from law enforcement who will sometimes set up sting operations and raid the player's brothels.
You've done a great job of factoring it all in to gear towards a grittier GTA experience. Bugger boat races and stunt trials, give me this.