I'm new to the game but I have been prospecting for deals for a while now.

House hacking in Chicago can be a game-changer—letting you live for free (or close to it) while building wealth through real estate.

There are several articles that do an exceptional job of explaining who, what, where, why and how tax payers qualify for the ‘STR Loophole’ listed here:The Short Term Rental Tax Loop Hole: A Game Changer for W-2 Wage EarnersThe Short Term Tax Rental Loop Hole: What Investors need to know The implications on the Oregon and California Coastal STR market is a strengthening buyer pool for luxury rentals in the $750-1.5M+ range.

You're way ahead of the game! 

I understand it isn't easy, especially when new in the investing game.  

He didn’t just answer my questions—he showed me how this game is played at a much higher level.

Also I have not worked out the financing yet. if I just use my cash then the Cash on Cash drops to 8 or 9% and that would be below my Cash on Cash target.Generally speaking and of course just numbers I picked out of the air for reference when running numbers in my head, I am looking for Cash on Cash greater than 15%, high probability of long term occupancy, and no expected major Capex for 2.5 years after purchase and purchase time repairs which I would add into the cash on cash evaluation before pulling the trigger.So there are some more details to be worked out in my head but being it is my first one and only learning what I could from youtube videos I thought I would get some feedback.With all that said, in my head it seems like it could be a good start.Thanks again Jaycee and Gavin for your feedback.

Just keep in mind the process can take a little longer since you’d need to work with contractors and follow FHA’s requirements.4.Your End Game: Whether you’re planning to stay long-term, rent it out, or sell once the work is done, it’s important to have your exit strategy mapped out.

Many are run by fake gurus who are just repackaging stuff they found on BP and repackaged as a get rich scheme that they sell by showing pictures/videos of people partying on a beach and things like that. 

He was very successful and wealthy before he started making videos and created a course.Does his course teach you to build a successful business or work hard at a W-2, earn a boatload of money, and then learn for free through a mentor like he did?