These areas could all be excellent long-term plays.

Excellent explanation!

Anthony id take your offer on meeting new contractors man are you looking to do more fix and flips?

I typically do pre-planning with clients coming on board to discuss their specific situation and formulate a plan.The best assets are receiving multiple offers these days and go quick.

That seems to have changed over Covid and not sure they ever got back on a regular schedule.Not sure what you have to offer other than the 4 bedrooms, but I would guess rent would be more around $2400/month vs $3000

Anyone contemplating the types of services some of these providers offer (sometimes into the tens of thousands of dollars) should first be able to articulate why the services are needed and how they will benefit from them.

@Brad Tull each of those markets would likely have something different to offer than the other. 

Areas like Pilsen, Bronzeville, and parts of the South and West Sides offer opportunities for value-add investments, while North Side neighborhoods provide more stability but at higher prices. 

If structured correctly, an S-Corp can offer significant tax savings while maintaining the benefit of rental loss deductions.

I suggest listening to the BP podcasts and reading through the blogs and books they offer.