0% chance.

So, the chances of someone trying to find the TRUE below market deal in their “spare time” is not great.  40 years ago you could.

Shayan,Best option to avoid issues and stay risk free along with having a better approval chance would be to go with a Cash out refinance.

And how can we align our approach to meet those expectations and improve our chances of securing financing?  

Hong Kong both chance for cashflow and appreciation.  

Many municipalities allow appeals, and the savings can be substantial if successful.Pro Tip: Work with a tax advisor or attorney familiar with local property tax laws to improve your chances of winning an appeal.2.

@Zach Denny - I agree - chances are the institutional lender won't be comfortable with an owner-financed 2nd and 100% combined loan to value.

@LaTonya Clark “One  can’t tell but I do know part of me is willing to take a chance”…You make it sound as if real estate investing is no different than gambling….

It likely would require something grossly negligent with huge consequences to have a chance to go beyond my coverage and we are not that negligent. 

There's a good chance it may not even appraise for what the seller is asking if the seller really is asking for that much more compared to others just for furniture.