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.

With your background in architectural design, you're already ahead of the game in understanding spaces and their potential!

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? 

Real estate is a LONG game and a good way to build wealth through equity.

As someone focused on wholesaling and sourcing distressed properties both on-market and off-market I’m always looking to align with investors, agents, and other fix-and-flippers who are actively in the game.

They wouldn't have any skin in the game and could just walk away and leave you high and dry if things go wrong with the property.

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

I am new to the real estate game and got my foot in the door by purchasing my first property as a live in renovation.

Throw in a few nice touches, like coffee or board games, to wow your guests.Keep extra linens, cleaning supplies, and essentials like toilet paper handy so turnovers are quick and easy.