I have a higher nightly rate because I can sleep more people, my taxes and insurance are higher.  

But, I assume it ultimately comes down to area and income class.

If yes, THEN we can talk taxes.You may be able to offset some of your W2 income with STRs.

Does anyone here have experience clearing a title after a tax sale in upstate New York and subsequently selling the property to a retail buyer? 

Currently, you could say we are both low-income; I'm a barista and he works in sales.

This is no different than taking advantage of a legal tax loophole. 

All your full documentation information (IRS taxes net and bank assets) are input and approval is a program, generally no exceptions to their rules.

If I want to use the STR tax loophole, would living in a different state affect the advantage of the so called STR tax loophole, as long as I remain active in managing the property and fulfill the other requirements?

I am considering two options for purchasing a A+++ SFR cash, Option 1 to place in a self directed IRA and let the IRA own the property and Option 2 is to buy in cash upfront and pay the taxes owed.I am 62 years old and have another five to seven years prior to retirement and so I am trying to set up my portfolio for income generation by that time.

A big issue you might run into is that most lenders will require you to qualify carrying two mortgages in your debt-to-income ratio.