I am now looking to enter the Chicago market, I have heard good things about that market.

And I also think that the inventory in your market plays a large role in deciding what property type makes the most sense.In my market, there is a large abundance of the small multi-family properties, especially the 2-4 unit properties.

If I put myself in the shoes of the outside partner/investor friend, I would be very concerned because: 1) unclear and/or potentially conflicting business plan, 2) even with clarity in the BRRRR business plan, unclear in the viability of pulling it off with these market conditions, 3) the chances of dispute seems very high, especially if you're going to live in. 4 years ago, I went through a  similar thought process when purchasing an investing property with mainly my family money, while considering an outside investor to rehab for higher STR ROI... 

I am not in the flipping market but I handle multifamily transactions for buyers and sellers who are very transactional.

Secondary Markets Are ThrivingOmaha and San Antonio are two examples of secondary markets where the cost of entry is still reasonable.

Are you buying amazing deals or are they closer to market value?  

I wanted to see what markets have both a relatively high rent-to-price ratio and high appreciation.

Currently, I'm analyzing different markets to see which one will best match my strategy.

Even the MTR market will start to be affected by this, right?

This is just bad banking practice and FTC should be aware of digital platforms like Baselane in many ways abusing their powers and washing their hands off.