Most professionals will recommend a separate LLC for every $1 million in assets but I don't think that's necessary.

However, one nice thing about this community is a one-time cost and it doesn't require additional payments.

The last event was a vape stuck in the s-trap of the toilet that required toilet to be replaced.

I think the height requirements in Chicago are 7'6" and we're right on the edge of that. 

It requires hard work, strategy, and a willingness to take on projects others might overlook.

Some states will give the underlying land while others will give the land but expect the newer owner to compensate the old while still others would require the owner to compensate the person who performed the value add.

I would recommend you begin researching Chicago based meetups as there are a bunch of really good ones.

Any referrals or recommendations for good and qualified brokers, sellers, property management companies, loan brokers, insurance brokers, mortgage brokers, contractors, etc.

Here's a list of things to track:- Formal lease application- Formal signed and executed lease specific to your state- Payment history (I recommend using online rent collection like Apartments.com, RentRedi, etc)- Maintenance requests and receipts- Accounting for all rental-related expenses (repairs, utilities, etc) The more you treat it like a business, the more helpful you are to your CPA come tax time. 

Depending on how it is done and what guarantees the government offers and requires of the released entities, interest rates could move slightly higher.