Free time: 100 Hours.
Cash on hand: $2000
Martial:
[] Take Martial Arts Classes: Cost: $50/month. Chance of failure: None. Time: 20 Hours. By taking a martial Arts class, you'll be able to refine your admittedly rough (but still effective, if the street fights you get into and walk out of on what seems like a monthly basis are any indication) fighting skills.
[] Buy A Gun: Cost: $500. Chance of failure: 30%. Time: 2 Hours. Buying a gun could save your life should you run into a person or beast on your travels who intends to kill you on sight. Of course, any person who doesn't know you well enough might think you're planning to become one of the many mass shooters that have infested the world...
[] Buy a Reliable Survival Knife: Cost: $250. Chance of failure: 10%. Time: 1 Hour. Sometimes guns run out of ammo, and you'll never know when you'll need a killing tool on your travels. No one wants to give anyone a knife he'll stab them with though.
Diplomacy:
[] Make a friend: Cost: Free. Chance of failure: 75%. Time: 3 Hours Although it's not likely you'll make one, it's still a good opportunity to practice communication with people who neither know you well or are paid to be polite to you.
[] Take Public Speaking Classes: Cost $50/Month. Chance of failure: 35%. Time: 20 Hours. If you aren't a perfect little charmer right now, then you might be able to learn to be one. It'll be difficult though, and you might not get anything out of the class.
[] Reconnect with Family and Old Friends: Cost: Free. Chance of failure: 20%. Time: 2 Hours. You have some college buddies you miss, and parents you wouldn't be too unhappy catching up on. Though they might not feel the same way.
Management:
[] Get a Job: Cost: Free. Chance of failure: 35%. Time: 7 Hours. Right now, you don't have a steady reliable source of income. You'll have to change that. Of course, you'll also have to convince people you're worth hiring.
[] Buy Survival supplies: Cost: $500. Chance of failure: None. Time: 6 Hours. You may very well have to spend a lot of time in the wilderness during your travels.
[] Take Wilderness survival classes: Cost: $50/month: Chance of failure: 10%. Time: 20 Hours. All the survival supplies in the world won't help you if you don't know how and why to use them.
Intrigue:
[] Pickpocket: Cost: Free: Chance of failure: 40%. Time 5 hours. While stealing is usually wrong (even if the victim can afford the loss), you need money in order to carry out your larger goals. Watch out for cops though.
[] Study Masters of Intrigue: Cost: Free: Chance of failure: 35% Time: 10 Hours: Despite your skills in the darker side of life, you wouldn't yet call yourself a shadow per se. By studying the tips, techniques, and lives of the great con men, thieves, and conspirators of history, you'll be able to further your abilities. Of course, you're not the best student, and you may have trouble getting insight from your studies.
[] Learn l33t Hacking Skillz: Cost: Free: Chance of failure: 35%. Time: 20 Hours: You're not exactly a computer master, and although you know what a BIOS is and why you need one, you're still far from becoming the Robin Hood of the internet. Taking some time to study not only hacking, but computer basics online could be valuable.
Learning:
[] Study Anthropology: Cost: Free: Chance of failure: 20%. Time: 5 Hours: From what you've heard about the subject, anthropology is the study of Human beings. While you have a feeling you're going to meet more things you can hold a conversation with than just Humans, its basic principles should be useful.
[] Study Language Principles: Cost: Free: Chance of failure: 20% Time: 7 Hours: Although you know that your power to travel to other worlds acts as a translator most of the time, for some reason, it doesn't always work. You have no idea what sort of languages you'll encounter on your journey, so a knowledge of what all languages share in common might help.
[] Study Learning techniques: Cost: Free: Chance of failure: 20%. Time: 4 Hours: You've never been the best student in the world. You weren't bad, but you weren't good. You knew even from an early age that what they were teaching you in school was mostly designed to create good little peons, and maybe that's why you never picked up on the better aspects of scholarship. Regardless, Learning techniques should help you pick up on knowledge faster.
Special:
[] Unlock and Visit a world: Cost: None: Chance of Failure: None. Time: Instantaneous
[] Go to therapy: Cost: $50/ Month: Chance of Failure: None Time: 3 Hours