Now, it's September and I really need to get it done because Covered California needs the California Return right away.  

You want to make sure that when you buy the property, the rent you will receive will cover all your costs (mortgage, T&I, maintenance, capex, vacancy, etc..).

All units are occupied and seems like they are all pre-screened by the current owner and are never late on payment.

Property management had found a tenant that met screening, and today tenant deposited $50 less than what was posted as security deposit.

Yes, you can screen them, get referrals, etc, but until you actually work with them and see them in action it is a big risk. 

@Tim Hocker  Keep in mind that your HELOC may very well be an interest-only loan  - so make sure your monthly payment is covering the actual debt and not just an interest payment. 

I am following the info in BP's guide to screening tenants, but I would like to know what experienced landlords do if you receive applications from multiple qualified tenants? 

You will need to supplement your tennat $2500 rent out of pocket to cover the expenses on this property. 

So the only question is, does the Market Rent for that location and Type of Unit cover the HOA, plus Debt Service, plus whatever other Expenses need to be paid..Because if it doesn't, the Landlord is in for a world of hurt!.

Together, we're a great team and individually we cover each other's weaknesses.