I have a ton of property management experience here in Chicago as well as a pretty large network.

Given experience, feel free to share where you would you start if you were in my shoes and if you're willing to have a further conversation to help me get going!

While I do not personally have a contact in KC, I'd recommend using BiggerPockets' Find an Agent tool.Its a FREE service for BP members like yourself who are looking to expand your network and find local experts.Here, you'll be connected with an investor-friendly with knowledge/experience in your desired location(s). 

Could you please share your experience of how you go through these obstacles and how do you choose your state and properties to invest in (if you are investing in tax deeds as well)? 

Your unfortunate experience is summed up in the word ‘trust’.

Finding the right team to assist you in your journey is what is most important, that way you have guidance, experience, and a partner that is looking out for your success in your investment. 

Initial budget $250-600k +- Please advice if it's seems like an ok plan in your opinion (preferably if you have personal experience). 

- Problem with compass is I believe they're too much investing into tech while it doesn't necessarily translate to bigger productivity and sales- The EXP model is actually significant changes where it tries to democratize the revenue by sharing it among team and leads- I would like to say the Exp is offering new business model in RE agency, while other agency is more like traditional where individualism performance is the key ; Same concept in used car you have regular used car dealership and you have car max which offer no haggle price.

As far as down payment, investment properties typically require a minimum of 20-25% depending on property type, FICO, level of experience, occupancy %, etc.

I am hearing you when you say you had the builder fix the grading issue, but grading is in my experience the #1 cause of repeated water in the basement.