You can influence property care as a landlord through inspections and a lease. 

As alluded above, if you don't have reasonably substantial amount of reserves sitting aside to bail yourself out, you could be a in tricky spot.  

Your hours are substantially long and 7 days a week when you first start.

But the additional cash flow from the STR business is substantial and it would NOT make sense for me to sell the Real Estate at standard valuation and give up the STR cash flow. 

Buying a property that has had substantial work done without permits is a HUGE risk.

Although I understand the desire to start big, there is nothing inherently more profitable in a 6 unit than a 2 unit building. 2# For liability purposes an LLC is good, but since an LLC is a pass-through entity, putting your property in an LLC is not really going to influence your tax burden (unless you have a multi-member llc). #3 As for areas, there are a lot of neighborhoods in Chicago that are literally built out of these large multi-unit buildings.

Perhaps a more substantial down payment would convince the seller to carry the note for a couple more years on the duplex while you rent out your SFH and get that rental income history?? 

One thing you'll want to triple check with your agent are the comps, it's substantially more difficult to comp multi unit vs SFR properties.

She explained that this wall would need to be painted and left white, though we would not be able to do it and so the property management company would charge her a substantial fee to repaint it.I should mention that I protested a bit, as the unit was scheduled to be renovated and so all of our cleaning would in the end be for naught.

He's a good, ethical, influencer who isn't too out of touch with his audience.