This is a numbers game.

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!

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 doesn't help with your tax issue but keeps you in the real estate game with a lot less headaches.

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

But it's in your interests to make sure the property value makes sense and the borrower has skin 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.

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.