A lot of times, these types of lifestyle choices will start limiting you down very quickly to specific areas, and since you are going to be living in the property, are likely to have a heavy weight on the neighborhoods.  

Have you thought about the specific strategy you are going to use or what your business model might look like?

The IRS, in a now discontinued Publication 535, used to say:If you are an individual and your attempt to go into business is not successful, the expenses you had in trying to establish yourself in business fall into two categories.The costs you had before making a decision to acquire or begin a specific business.

Anything specific in your plan or locality that would force this?

What specific roles do brokers hold that agents should not? 

Laws are super local, changing from one place to another, so it's a smart move to get a lawyer to tailor that lease specifically for your spot.

If you have specific questions or encounter challenges along the way, seeking guidance from professionals in the real estate financing industry can be beneficial. 

I know you will find a ton of encouraging and helpful people here.Regarding HELOC I suggest you connect with my good friend @Michael Barbari...I believe they can still do up to 90% which is 10% more than most banks.If you need any other specific connections here in Chicago I am happy to provide them. 

Pay for an area, industry specific listing with credit ratings below xxx.4. 

For your first unit, unless hiring outside management which means giving up 20% of earnings, you're going to have quite a hurdle to operate a place remotely.I don't necessarily think looking at market specific data around the country and thinking you can just dive into that market and do well makes much sense.