You should consult an attorney or CPA for your specific situation.ANONYMITY: When you create the LLC, your name is recorded on the documents and published on the Secretary of State's website for all to see.

Here's some hopefully, helpful cut & paste info:------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?

Not to mention the loss of income for 8 months, shutting down the business and many other trickling down financial problems because of it.  

Premium increases are rippling through the market; the state is also always going to be financially strapped/high tax due to union pension commitments from past generations and the high tax, high services nature of Chicago.I'd highly recommend getting on a plane and driving around before you buy anything there. 

You can also scrub public records to see who has recently bought in the area (if available) all cash, some of these folks are investors, hit them up too.

Once a month we drop off all the paperwork, they record everything in QB.

This is where a lot of people make mistakes and then keep those mistakes going until they decide to outsource it.Also, Tax Accountants can create Profit and Loss Statements but that isn't their specialty and they aren't focused on keeping your financials in order.

Every property of interest must be evaluated based on current and future performance.Current ConsiderationsTime to rentRenovation Cost & RiskInitial ROI and cash flowPurchase PriceMaintenance costAcceptable area rental restrictionsIn an area that is doing well and likely to do better in the future.In the migration path of urban sprawl.Future ConsiderationsThe location has a track record of appreciation and rent increases.It physically matches the expected demographic changes for the foreseeable future.Buy what your “customer” wants to rent, not what you think is a good property.

Many think it’s strange to be scared of success, or they make fun of me for it, and I don’t understand it myself.I genuinely want to be rich and financially free; part of me believes I can do it, but deep down, my mind or whatever doesn’t.

You could then get a HELOC/LOC on that paid of property (a product that doesn't require you to use it) and then if you did have a big emergency you had a line to use on it.Now, ALL of this is dependent on how much money you have in the bank, how many properties you have, what your income will be like in retirement, what the standard age would be for your end of life (that's a scary one to think about), and while yes, you can certainly take equity out I just think it would be good to sit down with a financial planner...or even some other investors that are local to you that are around your age demographic and see what they are doing.I'm glad you are thinking about this for sure.