I wouldn't recommend trying to do something like this right off the bat, I think you need to get into the game and really know what you are doing before taking on that level of risk.Happy to chat more over a phone call or direct message if you want more insights or have more specific questions!

This is a numbers game.

I am a fellow house hacker and think it's the best way to get into the game if your circumstances allow it!

Illinois requires a license to market aka wholesale more than one property per year.Are you looking to get into the wholesale game here? 

It's simple really.  

Hi @Shan Randall,Welcome to BP and congrats on stepping back into the landlord game!

If you work a day job in addition to your plans to pursue real estate in this way, then focusing in 1 city/MSA will drastically reduce your time spent focused outside your job, allowing you to keep your income high, your job safe, and your problems simpler.

If you told him you have been playing pickup games for the past year and need help improving your jump shot, now he has evidence you're motivated and a specific goal he can quickly help you work towards.

Changing the strategy can help get in the game. 

This also may be a good way to get an in working for someone with more experience since being a new wholesaler who doesn't even know where to start makes it very hard to start.Also, don't start telling people you are a wholesaler before you have marketing going out, a small buyer's list, and at least one property locked up because everyone wants to be a wholesaler, but it's not actionable until you are in the game.