Policy is going to be a huge factor.  

PITI & HOA fees = $25k per yrRents = $22k per yearLess management commissions, upkeep, cleaning and amenities.Leaves $15k per year.Runs in the hole $10k.Any tax benefits?

Need for additional liability protection, such as an umbrella policy, in any case, whether or not you have an LLC.

I am planning on getting 2 roommates to cover almost, if not all PITI.

If you have a no smoking policy, you need to enforce it.

But if I'm paying the full year in advance, why would my lender require me to make the additional monthly payment on the same insurance policy? 

Read every word in the policy.

Tax policies in some areas are favorable in the long term which means that a few years down the road you will not be taxed out of your property.Start looking in the $175-$250k range for good returns with less down.  

They never mentioned a timeline when I opened the policy so to me it was pretty shocking.

Another big factor of my when to sell was when the value reached replacement or rebuild cost as estimated by my insurance policy.