One thing that helped bring some ease to me was that before agreeing with this buyer.

If they're good tenants, they have a bank account, and would welcome the ease of paying online and automatically via Cozy, it's free.

An LLC would be the best for liability and privacy as well as ease of use but if getting loans you may have to personally guarantee the loans.

I don't know the ease of knob & tube removal at the triplex you're pending on but not all knob and tube situations cost a ton of money.I'd call a boiler dude to see how much it'd cost for an inspection.

Any chicagoland area wholesalers or buyers who can help ease my worries? 

This will ease any feelings of "intrusion" they may have and if not, that's their problem.

Why would one account look fishy and what account or source will typically put worries at ease? 

I have talked to a real estate lawyer but am not sure whether it makes sense to push up the tension that way.

I’m guessing your bud doesn’t really know what all is involved in getting to a closing......hence the ease in which he thinks he can simplify it.

Use PayPal, Square or Stripe to create simple services or products for your repeat customers.Use WiFi smart locks for ease and efficiency.