After moving out I was able to cashflow ~$1,000/month but ended up refinancing and getting all my money out of it, still cash-flowing $450/month, and using the money to buy me another rental property.

Ultimately I achieved an infinite return on my investment: without having any money in the deal I flow roughly $450 monthly and have around $100K equity in the property.

@Alex JacobsBuilding a rental portfolio through house hacking is a terrific idea, particularly if you want to reduce your down payment and increase your income flow.

Bottom line would have me cash flow $800-$1000 after all said and done.2.

You'll pull more money out, but have a higher mortgage payment and less cash flow, so it's all about what you want out of the deal.

You can still cash flow in some areas, but it will more than likely be in D class neighborhoods. 

I don't need cash flow right now, I'd be more than happy just living for free and getting equity in this market. 

From what I read, you have the solution already--with the cash flow and equity, pull out some cash from a property you already own either by cash-out refi, or HELOC. 

It is a deductible expense but if you are focusing on cash flow Indiana is good, Illinois bad.

Here in Houston most of the 2 to 4 units are around Downtown area and if you want to find anything that stands a chance at cash-flowing after you move out, you pretty much have to look in the east side of Downtown.