When there is a turnover, there is more work, but usually there is a placement fee which covers the extra leg work she has to do (placing an ad, doing showings, move out inspection, making sure utilities are transferred, etc).

I talked to an architect today, he said he can take original plans and transfer it onto a permit plan sheet.

Makes it easier when you want to transfer information or allow access to someone for book keeping or taxes

A contract or receipt is suggested to show the transfer of property. 

One transfer of money from a personal account to an account associated with the property and you're toast!?

Life happens.You could try and coordinate the work times between the handyman and the downstairs tenant, but I think that would be impractical for your tradesman. 

I already understand that MN and my home state OK have license reciprocity, and know what the process is to get it transferred over.

I am not sure I buy that Pilsen is the one southside of Chicago neighborhood driving rent increases, but it is surely a gentrifying area and factor.I think Bronzevilles & Woodlawn's ability to have more new developments has allowed that entire se coordinator to become a huge factor on the southside.Regardless, whatever you are doing is working so keep doing it!

I opened a business checking account, transferred money from my own credit union account and then was told the new business account was being closed and that the bank was holding my money for 60 days.

It should also be noted that this permit is transferable in a Real Estate Transaction, so as a buyer or seller it is always going to be important to make sure this permit is in place from this time moving forward!