I would do this annually for all units.If there is someone there you initiate a dialogue.

Let’s say you have $54,000 cash for down payment.With 20% down payment you can afford a $270,000 propertyYour monthly expenses will be $1,160 mortgage +taxes$333+home insurance $100+$HOA fee $410=$2,000Annual Property expenses $24,000 a yearIf you keep your condo occupied 7.5 month a year your revenue will be $33,000-$36,000 minus $24,000 expenses Annual NET $9,000-$12,000.I hope that helped.

I have explored the option of investing in stocks, namely low or no-cost index funds/ETFs, that would provide a respectable annual return.

My annual cash flow would be $2,400 but I wouldn't pay a nickel in taxes due to depreciation and this will show up as a paper loss in my income tax.Say if I held the exact same property under a LLC.

(see point2).2) if you had a shortage in your prior year escrow, you will be given the opportunity to rectify the shortage, if you don't, they will annualize the shortage and that will be added to a NEW calculation.So say you were paying $100/month. 

Any Wolf-dog hybrid.2.

In my town, 5 or fewer unrelated individuals living in a house is just a $30  fee annually and a house inspection every 3 years, no special permitting or requirements like sprinklers, etc. 

It doesn't literally destroy your annual cash-flow.2.)

I'm new to Bigger Pockets, too, and I travel to Oxford for the annual William Faulkner conference, and love Oxford!  

@David MorganIn my personal view, i is generally best to just hold the beneficiary IRA at a company like Fidelity investments and invest in stocks and mutual funds because of the fact that you have to take annual distributions.