The real issue is it might cost you 1.5% more in one time closing costs to get that extra 5%. 

.—(1) The commission may deny an application for licensure, registration, or permit, or renewal thereof; may place a licensee, registrant, or permittee on probation; may suspend a license, registration, or permit for a period not exceeding 10 years; may revoke a license, registration, or permit; may impose an administrative fine not to exceed $5,000 for each count or separate offense; and may issue a reprimand, and any or all of the foregoing, if it finds that the licensee, registrant, permittee, or applicant:(h) Has shared a commission with, or paid a fee or other compensation to, a person not properly licensed as a broker, broker associate, or sales associate under the laws of this state, for the referral of real estate business, clients, prospects, or customers, or for any one or more of the services set forth in s. 475.01(1)(a).

Good investment focused agents spend the majority of their time finding good deals, giving you guidance on strategies, and making your offers competitive.

The work should have only taken 2 o 3 months because there was no major construction work done to the home except the metal roof and an HVAC.We brought the property because these friends have several section 8 properties in the area.

In my rental agreement (lawyer reviewed and approved) it specifically says no smoking or vaping within 20ft of the building and all butts must be left in a coffee can with sand in the bottom and one is already provided in the "smoking area".Explanations are given for allergies, health, and second hand smoke etc. etc.I've not had any issues yet.

That can cause all sorts of tax issues.

It doesn't work that way for the vast majority of people.The average new car payment in america is $726, that's crazy to me. 

If money wasn’t an issue, we would buy rentals closer to home or back home in Florida which is where we ultimately want to settle down in.

Then I assume major damage, just to be safe if he won't allow an lookee see first.

Chicago and it's suburbs are notorious for multifamily zoning and illegal units issues.