Registering as a foreign LLC allows you to maintain continuity with your existing business structure, branding, and EIN while operating legally in the new state.

Use a buyer's agent that knows the market, contracts, negotiations, etc.If you really want to learn about investing, get a job in property management. 

If you're willing and able, I do recommend the "house hacking" strategy which is just a fancy name for buying a rental property and living in one of the units, because you'll get very favorable financing - an owner-occupied fixed-rate 30-year mortgage.I'd also say, analyze that property as if you won't live there and it's a pure rental, and make sure the property is still cash flow positive if there's a tenant in your unit because then you'll know if it's actually a good investment.And when you analyze it, include payment of a property manager in your #s because if you don't, and doing so would make it go cash flow negative, then you've just bought yourself a job because you literally can't step away from managing it without losing money.

Just go ask Steve Jobs. 

To avoid non-competes and make twice as much, I wouldn't be getting a W2 job initially in Chicago and would rely on 1099 income.

I have a great job that I love and currently do not need to spend the cash flow from the properties. 

I learned from Dave, how to talk to potential investors, how to build rapport, how to answer questions and explain the company’s strategy and operations and the secondary mortgage industry.

Quote from @Steve Wortman: Currently the owner operator of a motel.

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.

Despite the house being operated for years by the prior owner as a STR.