I’m 18 fresh out of high school, I’m trying to start a real estate investing company and I need a lot of guidance, any help is greatly appreciated.

Due to horrible, and I mean horrible property managers in the area (the one known as being the best admitted to me she recently had an employee steal over a million from landlords and she didn't think it was her fault), I decided to hire a family member full time to start managing properties for me. 

Managing tenant relationships is crucial for us landlords and real estate investors.

8-months later, have you managed to make any progress?

I realized the grass wasn't greener, and I ended up building back in the Chicago area once again.

Bob is right that you can get better cash flow on the east side, but I still see deals pop up over there from time to time and I don't see any rapid depreciation in those neighborhoods coming any time soon and I think if your strategy is to buy and hold in nicer areas with less risk, it's a very good area to target.

My wife and I had a loss during 08 meltdown, so she now against investing.  

obviously 150 doors on conventional loans for each would murder you so I assume that is the case and the 8 doors listed are just examples. at 150 doors you need to start talking to fund managers or heavy hitters in the multifamily space.

Can I create an LLC just for running the Biz/managing aspect, but not transfer my property into the LLC?

I haven't set specific targets beyond this initial goal, but I may aim to increase my passive income to $5,000 or $10,000 per month in the future.Current PropertiesI currently have two properties:The Loft:This property is rented out long-term and generates around $300 per month in passive income after HOA and management fees.The loft has approximately $100,000 in equity.The House:This is a brand-new build (2024) that I'm currently occupying through house hacking.I invested $70,000 in the property, which means I have $70,000 in equity.My plan is to convert this property into an Airbnb or long-term rental within the next two years.Short-term rental comps suggest I can earn around $3,500-$4,000 per month, while long-term rental comps indicate I can earn around $3,000-$3,300 per month.Seeking AdviceGiven my upcoming financial situation, I'm seeking advice on the best course of action.