Just be sure the deals/flips can cover the financing and holding costs.

While private land is not my area of expertise, it would make sense to me that if the rehab covers certain areas of the home, the answer would be yes.

Contract states 5 years and after that tenant would need to seek own financing for purchase payments made will only cover interest and taxes no principal.

They do not cover for such cases; "I have confirmed that we will not have any options while you have a tenant in place that you are actively trying to evict."

We missed several increases over missing lightbulb(s), broken screen(s), or a tenant decision to removed copper overflows on water heater (scrap value)... 

He makes very little, and I don't really need to worry about his credit, because his brother / roommate makes enough to cover the rent.

I was thinking of purchasing a plex and live in one unit and have the other unit's rent cover a good amount of the mortgage.I've been getting some mixed signals on buying vs renting, and hopefully some experts can share their insights on it.Some of the arguments that I've received for renting first is:I don't really know the areas in Seattle, and buying a property will lock me down in a long and big investment.

The cost of repairs / rehab is absolutely outrageous in most cases and  usually does not cover by a small pet deposit. 

We make residential and commercial windows and doors that covers the east coast and Bermuda.

If you don't need the equity i would look at renting if possible or doing an owner finance deal on it with higher interest rate to cover the underlying lien.