This is one of the biggest insulation issues second only to the attic.

One of the biggest time sucks can be finding & screening a tenant!

With that being said, the interest rate is going to be the single biggest determining factor for whether you're barely breaking even, or seeing a decent monthly cash flow.

But in my opinion, the biggest issue I see with folks jumping into their first "big" multifamily deal is the quality of the pro forma. 

I like option 2 to diversify the investments in 3 smaller rental propertires, 3/2 around 1500 sqft, in good school districts which will open the biggest pool of tenants. 

Biggest thing is cash position.  

Using different colors was one of the biggest mistakes we ever made in the early days; tracking the colors even with a spreadsheet was a nightmare, as was keeping dozens of different touch up colors in the storehouse. 

My biggest rule it to pay off the heloc as soon as possible because the rate is variable and its much safer to be in a locked in mortgage.

Parking will likely be your biggest hurdle.

Your comment does bias me slightly in favor of Indy, since at least we're talking about a manageable car ride.That said, I'd love to know the biggest mistakes you've seen - how do neophytes typically "crash and burn?"