A little about me for context: I live in a very expensive market in Rye,NY. 

Because if you need to live off the cash flow what you're really looking for is a business. 

The wear/tear is much less for STR because the guests do not live their full-time.   

Financial freedom isn't simply about replacing your current income, because inflation continuously drives up prices, making a fixed income insufficient to maintain your standard of living.

But this was an awesome opportunity for me because this is my first living situation where I will be on my own (and getting used to paying a rent/mortgage) but this will put my overall mortgage on a 400k house at roughly $2000 a month for the first year!

Quote from @Jay Hinrichs: Quote from @Engelo Rumora: @David KanarekI don't think I have ever seen better investigative research than this.Hat's off to you and sorry for your troubles and everyone else's.Please don't investigate me haha Engelo as someone that has taken this kind of abuse on BP and SM  and lived to fight another day I think you understand better than most investors mind set and how they feel or attack if their deal does not go right.  

@Isaac TerryIn terms of it being worthwhile, just like most other markets out of state if the barrier or entry is too high where you live, the landlord laws are not favorable where you live, and you are looking for positive cashflow then Cleveland can be a good option.

Any sober living investors out there willing to let me pick their brain on how to underwrite a potential deal?

Living in top unit and renting out the bottom.

After 25 months, If they can prove that they lived in the property for two of the past five years, they can sell it as an owner-occupied residence.