Just a warning, this au strays a bit close to NSFW territory in that it does talk about Sex Workers, but it does not mention or describe anything specific, mostly just discussing how they operate and some dangers they may face working in Gothem.
So, we all know that Tim would do a lot for the mission right? More than most people would. I mean, just look at Brucequest or the fact he came back after his 16th birthday or his first few months as Robin when he was basically Bruce's nanny. He also has many false life's he can slip into at the drop of a hat such as Alvin Draper or Caroline Hill. So why not add one more to those personas? A woman named Jane Doe, a sex worker who works just outside Crime Alley who everyone knows and knows everyone, but no one truly knows her nor have they ever seen her face, if she even is a woman as she uses all pronouns to get just a little more mystery added to them. Their outfit is constantly changing but also very specific, a short and highly attractive dress that doesn't look cheap and a full face mask in the style of Venetian Carnival Masks, Volto design specifically so that it covers his full face but shows striking blue eyes. Those he has colored contacts that he switches around constantly.
The reason that Tim does this is simple. Information. While Jason may be able to ask the sex workers under his protection questions, they wouldn't be as open with him as they would another sex worker. Tim can get information from them, the clients, the shop owners of the area, the homeless, anyone and everyone who is often on the street or connected to it that none of the other Bats would ever be able to get. And through his... services he gets a lot of information about up coming things thanks to a special discount everyone knows about. If you tell Jane a secret they don't already know, you get 10% off his services. Tell him 2 and you get 20%. So on and so forth, but it has to be things that Tim didn't already know and he's more than happy to hear about which rouges are hiring at the moment and when they stop hiring, after all, what easier way to predict when they are gunna do stuff than by when they get new henchmen?
A lot is known about Jane Doe, yet also nothing is known. Jane doesn't keep any of the money he makes, giving it to the other girls and often extra as well. No one knows where she keeps getting 100s of dollars to just *give* them but she does. Jane has three brothers, a sister, and a father but no mother. They don't know their names, simply knowing them as N, H, C, R, and B. Whoever they are, they're a well off family but they aren't good to Jane, bad enough that Jane feels safer on the corners of Gothem than the comfort of her home. They know from "funny" stories he tells about his family or via them asking about scars he forgets misses when he covers himself in makeup (there are so many, what have they done to you child?) And him always telling something close to the truth.
They know that N is his oldest brother and the only one who cared about him for a long time, who helped him and was the first person who ever made him feel truly happy. They also know that N took something very precious from Jane Doe without Jane's permission and shattered their trust in N. Tim never told them what was taken or that it was Robin, but in a profession like the one he shares with them, they all come to the same conclusion about what was taken and why Jane might seek comfort in this line of work.
They know that H is also his older brother and has hurt Jane often. They know that the slight scar on his neck he covers with a choker or makeup was made by H, as was the bullet scar in his leg. He laughed about that one, telling his friends how H had set down one of his guns after cleaning it, R picked it up and accidentally fired it, and it bounced twice before going clean through Tim's leg. He laughs about how mad H was at both of them and how he yelled at them to not tell B or else, using a mocking tone and laughter that only causes the others to glance at eachother in worry over their friend. Tim makes sure to reassure them that he got to the blood before it dried so it wasn't to hard to clean up. Tim may have read it as anger in Jason's voice when he said to not tell, but actually it was panic and worry about Tim's wound and how Bruce would react.
They don't know much about C, only that she managed to escape the hell hole known as Gothem and lives in another country. Sometimes she comes back for visits and Jane is always very excited when she does.
The other Sex Workers don't like R. They know that R has either threatened Jane with sharp objects or actually harmed her with them many times but has never gotten in trouble for it. Any time Tim has some left over injuries from patrol, he plays it off as either R or H getting agressive with him again and tries to calm them by saying, "oh come on. Both of them have only tried to *actually* kill me twice! It's fine guys, they won't seriously injure me." While having 5 stitches in his arm.
Jane doesn't talk about their Dad much, always getting quiet and looking away when he's brought up. They ask if B has ever hit him and Jane says, "he doesn't hit me anymore." And all of them want to kill him. They want to kill all of them (except maybe C) and bury their bodies where they'll never be found.
Of course, none of the Bats know about Tim's other nightly activities and where he gets his info from, simply shrugging and moving along. Tim is terrified of any of them accidentally finding out. But unfortunately that day could be coming soon as one of the workers goes to The Red Hood and grabs him by the jacket saying, "you're supposed to protect us right? That's what you promised us, isn't it? Saftey? Well one of the others, Jane, is in deep trouble. Their family is gunna *kill* them. Do whatever you need to do to keep Jane safe from those monsters, we'll tell you what we know, but stop them before she's just another dead body in Gothem Harbor. Do we need to pay you? We'll pay you however much it takes for you to make them pay."