For instance I had a special case where I billed the tenant an extra expense monthly on top of the automated rent collection, so I add it as an expense and it would automatically email them and notify me when it was late of course.

Be prepared to invest extra cash into amenities to lure guests in.

Your boss basically has to mentor you AND you get extra repetitions in building your experience in the business. 

Renting to a Section 8 tenant can take extra time to fill out the forms, pass inspection, get approval and move the tenant in.

  $800 per month for 12 months, $9,600 extra cash and profit for sending some letters out. 

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

We are concerned that the smoking/smell will turn off prospects as well as the extra cost of cleaning up areas after smokers move out.The building is in Illinois. 

It may sound nice to pay a 6% management fee but the extra fees can add up to be more than the other company that charges 10% with no additional fees.

So I should not be paying any extra taxes.

That's an extra $16,500 for next investment i.e buy a property with extra $66K price tag.