What would be the biggest challenges or hurdles to making it happen (e.g. infrastructure, safety, government support)?

As Gino stated, I think the biggest challenge will be financing with negative cashflow.

Go look 50 years ago who the biggest companies are.

This might be a workable scenario for me.Lack of experience would not kill this deal for us but it would depend on a few things.Usually the biggest challenge for newer investors is in the amount of equity you have available to infuse into the project.You need to have a cash down payment to secure financing.With 25% Down you would be in a multiple financing offer situation where we're just fighting to get best deal possible and batting off Wholesale Account Execs left and right.

The biggest thing will be showing the upgrades you've made to push ARV. 

That's my biggest concern.

I THINK adding yourself to the title is the biggest tax mistake possible.

The biggest take away-Always maintain control.

Miami just had the biggest rain event in history without wind damages.

One of the biggest drivers of any percent rule is how high the rent/Income is.