Thank you for the extra thoughts to consider and advice – really do appreciate it and trying to take in as much info as I can right now!

And even if you don't say it is $50/mo, does paying an extra $10-15k or more to avoid that worth it when that cash can bring in more cash flow and equity gain from other properties or investments?

As far as appliances and “extras”, we’ve really scaled back over time.

@Stephen DeFalco Chicago is an enormous market, and I think you should start with the end in mind here.

After remodel They sell for only $3.8m, you get your $600k back plus $600k (much bigger than your assignment fee) and your friend/seller gets and extra $600k in their pocket making you buddies for life.

That could mean extra capital outlay to attract a tenant. 

And yes, $1 a gallon more is just x more, but at what point does that extra dollar become significant. $2 to $3, $3 to $4, $4-$5 etc, eventually it matters. 

The LLC plan to avoid lawsuits is a construct from people who charge to set up LLC's which fails to tell you: annual fee for LLC filings, extra costs for extra tax returns, total need for an advisor CPA.

I know all this because recently a repair was done in both units, and the one apartment is nicely kept, and the other apartment is not nicely kept at all and they have an extra animal.

If you can pickup a $250k house with an extra bedroom you maybe in the $2k rent range.