Tenants who are unwilling to set up auto-pay is a sign (at least to me) that they may be late on payment and don't have sufficient funds. 

Last year, I was personally quoted $7/mo. for basic limits because of a multi-line discount from my auto insurer.

All accounting is moving to the cloud and Xero will auto categorize your bank feed and makes reconciliation really easy.  

This could be actual $ out of pocket, example, you hired a bad contractor and needed to have the work redone by a 2nd contractor.Or a loss of realized income, example, unit has been vacant 6 months and you should have had it rented in 1 month.Additional Coverages/policies you should consider carrying as a PM to protect yourself and your clients,General Liability - Work CompCommercial Auto- Hired and Nonowned

The 8 plexes on Clark (Cameron Village) are mostly condo conversions now.

From Ukranian village to Logan Square/Bucktown.

A couple of quick follow-ups:1) The person I met does not use leases -- just straight month to month, and he uses an auto-pay CC system.

Auto pilot program.

If you do not have your NOA for 2015 yet, then bring a copy of your T1;If you have investments, including registered accounts where you are the beneficiary, bring recent account statements;Bank statements showing your account balances for the past 2-3 months;If you have recently changed jobs, or received a promotion/pay increase, include 2-3 months of pay stubs and/or a confirmation of income letter from your employer (on their letterhead).If you have any debt - student loans, auto loan, credit cards, LoC, etc. - include recent (last 2-3 months) statements for each.If you have any court ordered payments -such as child support or restitution - bring a copy of the order and recent receipts;If the property you are purchasing is a residential rental property (1 - 4 units), bring copies of leases - or Estoppels - for all presently rented units.  

I have a tenants that has requested an auto draw set up on her account.