Regarding BRRRing OOS - it can be very dangerous:(Too many newbies take contractors and agents at their word, when "trust, but verify" is extremely important.Given you're in Chicago, would recommend you plan 2 trips for a BRRRR:1) Initial walk-thru with contractor(s), which you should video for documentation & accountability.2) Final walk-thru BEFORE paying out final amounts to contractor(s). 

There are tons of articles and Youtube videos to help you with setup and monthly management. 

I love there YT channel and informative videos but dear god it's just a LLC!

And there are real estate text books, many used in business schools, as well as building trade books, magazines, youtube videos.

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

I will provide more information later.The two main setups are:1- Holding company in Wyoming if I want Charging Order Protections advantages, then a Series LLC in Kansas holding my Kansas RE and another Series LLC in Missouri holding my RE in Missouri.2- Holding company in Wyoming if I want Charging Order Protections advantages, then form as many LLCs as I want inside of it, one per rental or one LLC per 2 o 3 rentals.Fees are pretty reasonable and the same as they disclosed before the appointment, on their website or youtube videos.

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

Warning: This video is GROSS.

Consider creating blogs, social media posts, or short videos on:•How to handle late-paying tenants•What to do if a tenant damages your property•Best practices for tenant screening•How to legally increase rent without losing tenants•By answering common landlord headaches, you’ll attract leads who already see you as a trusted expert.4.Market to Investors•Many property investors want a one-stop shop—someone who can help them buy, manage, and eventually sell their rental properties.

#McCormickI have some Youtube videos (link in my profile) that will help with some of your questions and I'd be happy to have a call to help walk you through the market and what you should consider when looking here.