A knowledgeable real estate agent and property manager with local market expertise can help you navigate neighborhood dynamics, connect you with contractors, and even identify off-market deals that fit your strategy.

Honestly, it seems like you’ve got more skin in the game than I do since I’m just getting started as a bird dog, but I really admire your approach.I think your focus on tax-efficient strategies and building a reliable team is spot on.

My resources and skin in the game is being allocated to the remaining balance of X purchase price.What path do you recommend in this scenario? 

Most Florida markets will share some dynamics though like taxes and insurance. 

TIAHi Dawn, regarding your occupancy, with in effective dynamic pricing policy, you should still be able to beat the market while weeding out “bad” guests. 

It can be a long process over time with multiple dynamics you have to be on top of consistently.

What does the family dynamic look like? 

With a dynamic real estate market, diverse neighborhoods, and high rental demand, Chicago is a fantastic place to invest in house hacking. 

A borrower really needs to have at least some "skin in the game" to make lenders feel comfortable.

I got thick skin and can handle just about anything without it bothering me, but I dont want you to be ANYWHERE in the circle of my life.