I made check boxes to be checked for different repairs and uses the repair levels for the costs.The same workbook also tracks properties cashflow, expenses, and repairs and allocates them to each associated rental as I enter them into one worksheet.

Yes, document it - and you will want to do so every time you enter a tenant-occupied unit to protect yourself from claims and to document your proactive maintenance/care of your property. 

I went to the county's property information management page and tried to enter what I thought was the parcel number (13 numbers) and it tells me the parcel doesn't exist on the database. 

The tenant has told me that the landlords father has entered her apartment on several occasions without notice.

Building upon what Sam said about multifamily and industrial prices dramatically increasing, the heavy flow of capital entering those asset classes at this stage of the cycle is affecting Cap Rate spreads.  

Since you're already in Naperville, I assume you'll be able to find the time to get around meet local RE folks and pound the pavement to find deals.That said, from my own perspective IL/Chicago have some serious challenges over the next RE cycle (or two) that in my opinion make it imperative to have well-defined exit strategy before entering any new deal.

Like most college students that enter the working world, I’ve now realized that I do not want to continue in my current job for the next 5-10 years and beyond.

When I had a number of mortgages to pay, the monthly mortgage payments consists of a number of debits, and a number of credits, so I press one button to make all the entries for each transaction, and you can have it scheduled that'll automatically enter it when you open up QuickBooks.  

Additionally, I can't think it would be very easy for them to find another landlord that would offer them a month-to-month lease.Finally, you mentioned "annual" leases, just to be clear I would enter into multi-year leases to the extent that they make sense with your business plan for your building.

Possibly passing on some guidance from a newbie attempting to enter into a huge market?