If the net amount that the insurance company is offering covers the costs of repairs, is there any point to go afterthe security deposit or involve the tenant's insurance company?

How is the earnest money deposit handled on each offer?

Is charging first months rent, last months rent, and security deposit overkill?

New lease or not I would get a written agreement from the seller and renters on the security deposits.

Going and depositing birthday money, and growing a savings account is an important lesson. 

The repayment terms for a 401k participant loan are equal monthly/quarterly payments of principal and interest (typically prime plus 1%) over a 5 year term (longer if used to acquire your principal residence).Please note that if you take a full $50,000 and then pay back the loan, you can't take another $50,000 until 12 months after the first loan was fully paid back.Per the loan offset rules that went into effect with the 2018 Tax and Job Act: if you leave your job and the loan is current at the time you leave your job but then the loan goes into default because you left your job, you will have until your tax return deadline (including any timely filed extension) to make the loan current by depositing the outstanding balance into an IRA (and thereby avoid the taxes and penalties that would otherwise apply).Please keep in mind the multiple loan rules:Under those rules, the sum of the balances of a participant's outstanding 401k loans under a single 401k plan (using the highest outstanding balance of each loan over the last 12 months) can't exceed 50% or $50,000 whichever is less.

Or, perhaps you should ask the person who made the comment.There is another qualification method which looks at your gross income via the deposits into your bank. 

For example, you buy the place and the tenant could claim the Seller allowed them to paint the walls black or that their security deposit was twice what the Seller claimed.

Hi Chicago, For all the Chicago landlord out there, do you guys do Security Deposit or a non-refundable Move In Fee (Admin Fee) ? 

We take a deposit for last 45 days of water and monitor the bills.