Can I charge him my late charge which is currently $100 after I get the rent on the 19th? 

A little background though...last spring we finished a long renovation by mid-May and didn't get the house listed on AirBNB and Vrbo until early June, which was much later than we were planning, and we still filled the rest of the weekends for the summer.  

And once I finish the due diligence, my work is done: it's completely passive.

We do not have any bookings until late November, but want to keep the schedule open for potential revenue.

Hows the Akron market been looking lately? 

In your case, you might have to finish the main units before applying for the ADU. 

However, tenants have not been great, basically late on rent and/or leaving repairs that eat all profits.

I payed the $1,800 for it a few years ago and started it but life got me distracted and I didn't finish trying hard enough. 

Get to the finish line on a property and be proud.

DSCR loans are long term loans that require the property to be fully finished.