Free online payment options are available or you could have the tenant set up direct deposit into your account for free.

I have homes that I have been in/to once in the past year, and the total time commitment for them has been checking the business account once per month to be sure rents were deposited properly.

Executed means signed and dated by all parties and the security deposit placed into your bank account (and they will need to verify this as well).  

I already paid $5k down as a deposit, so the amount of the total loan without financing fees etc should be about $97K.

Many landlords in Chicago are not taking security deposits because they can be sued and lose something like 3x the deposit.

Obviously I wouldn't want to go near Casino road...any other advice for that area? 

The dress code is the same when you are looking at houses as it is at Casinos or Neiman Marcus. 

They also absorb many expenses that the tenants could take on, such as a few utilities, background checks for applications (they pay a lot for this a year), and damage out of deposits at year end.NOI under new management could near 70k with savings for 7% vacancies, 7% repairs, and 4% CapEx (due to many apts in just 2 buildings).I'm interested in trying to figure out how to schedule a payback period in excel, if anyone has number crunching experience with that for 1) the loan, and 2) the investors downpayment.

How would you recommend handling the move-out inspection and return of her deposit?

@Tarold Davis1 (lining someone else's pockets) and 3 (non-refundable deposit, higher than average rents on a house you may or may not purchase) waste money and you don't own anything.Option 2 gets you want you want for your kids and doesn't tie up your money.