As you begin your RE journey might I suggest using this website as an easy go-to.

I clarified and re-clarified what I wanted.

Yes if the cost is merely $7k, you will be able to re-capture that cost within 1 year and most importantly, increase the value of the home. - What measures can landlords take to ensure protection while renting, and what steps should be considered prior to seeking a tenant? 

We intend to gift properties and money to our heirs and they can be investors and landlords or whatever they chose to do.Not sure I really want a financial planner telling me what I am doing is screwed up, but I will listen to other RE investors and any good ideas they may wish to share. 

Regarding Chicago, the 2024 property tax re-assessment in Cook County should cause some inventory to hit the market, specifically on the mixed-use and multi-family side of things which will be hit especially hard.

Being surrounded by like minded individuals, whom are at all levels of their RE journey, is amazing and you can learn so much from all of them.I am on the lending side of things and would be happy to hop on a call with you anytime to discuss financial strategies and help answer any questions you may have about nearly any loan product available to help you on your journey, even if they are not products my capital partners offer.We are all here to help you learn and grow.

Holding RE till death is always great in theory but reality makes it so much more difficult.   

You can hire a RE lawyer to oversee my  side of the contract if I really need to.

Just like you I have been thinking into mentorship programs and I have gone to Multifamily Mindset ($40K), Apartment Educators ($20K) which is based in Texas, and now I am looking into RE Mentor (mentor of co-founder of Multifamily Mindset) and it's a 3 day seminar for $1500 (but they end up giving you a *one time discount* if you sign up during the free 2 hour event for $995 but it is possible to sign up for their mentorship program through their website if you can't go to their free event).

In my opinion, house hacking is the easiest way to get into the RE game with the lowest money out of pocket...plus if you throw in a renovation loan like the 203k or homestyle, you can boost your worth quickly!