The roof looked to have darker spots on portions of the roof but the description says "newer roof" etc..

Even though you paid conversion taxes when you rolled it from pre-tax/traditional 401(k) to Roth IRA, if you're under 59.5, you still have to worry about the 5-year rule on the earnings portion, I believe.

Every good borough has its less desirable area (next to sewage treatment perhaps) and every bad area has its safer portions. 

We paid the loan off in just over 2.5 yrs and that cut out a good portion of the Interest on the life of the 5 yrs loan.

Assuming you could get loans, you would still have to pony up the equity portion/down payment. 

Otherwise, run the numbers as you would for any other investment property.For renting, make sure that you find places with enough wiggle room in cost that you can have your roommates paying your portion.

For fix and flips, where I will be an investor only, then sell the house to a buyer, then pay my partner his portion of the profit.

We do have permanent financing products to do the hold portion of the transaction.  

I am currently looking to buy a property to maybe live and rent out other portions of the property for cash flow...but realistically, is that even possible?  

@Daniel Elijah Richardson, in my state, it cost $85 to take the test initially - both state and national, and $80 to retake either portion of it.