Track recordWe see instituational "sizers" on how they price loans and can say they grade you by your credit score, your experience, the LTV and property financials.

But, given that he has a primary residence there already that he must leave (Army doesn't give much choice on location), if he isn't able to sell the property quickly for at least break even, and can't take a deduction for a loss, my thinking is to flip it to a rental (question is which kind makes the most sense), he should be able to cash flow given his monthly expenses, even if only $100/mo, then if he still sells for a loss in a year or two, he could take a deduction.  

My goal is to achieve financial freedom by age 36 and to understand various aspects such as investing education, strategies, business planning, properties, marketing, and exit strategies.

I am only financially responsible for the utilities and have never purchased a property in my personal name (which was discussed with the lender prior), I have only bought a few fix and flips in my business name.

With limited time I have in US, I have some financial targets to meet, one being scale and increase my net worth.

., selling at a loss or using a 1031 exchange).

Either can work, or either can be a huge pain, but that's the reality of common area ownerships.I've worked on some small 2-3 unit condos like this doing the condo plans and the CC&Rs have always included provisions for financials, budget etc. as well as dispute resolution.

“Section 3: Financial Information — Real Estate.

The IRS in its Passive Activity Loss Audit Technique Guide published a sample Activity Log.  

For most people you will only save a little money on any PROFITS if you have a loss the first year.