The cap rates appear attractive at first glance, though a thorough analysis of the local markets is essential, especially the long-term vacancy rates.

Is this essential?  

I spoke to a loan servicing company today (found them via Pace Morby YouTube video) and they confirmed that this doesn't help.

It is fairly low-cost and efficient (you can always scale your entities as you grow; there is no need for an ultracomplex structure at the outset), but it is essential to ensure that entities are appropriately maintained. 

I will essentially be managing the entire property/collecting rent and my friend will not have to lift a finger. 

Capture the most accurate photos and video walk-through of the space as you possibly can.

Contrary to how youtubers glorify the profits, property-flipping is essentially a value-add/opportunistic strategy and the key risks you, as the investor, are taking are 1) asset prices, i.e., how well will the market be when you sell the property, and 2) capital expenditures, i.e., can you financially efficiently improve the asset to the end users (renters or users).

I just posted a video on YouTube on certain neighborhoods in Chicago and there are some neighborhoods where the prices are falling or staying longer on market.

If you can do that then you have answered most of your questions - essential skills, client relationship, exceeding industry standards, etc.

The video is both a great message and approach.