One of my business partners back in the 2000s was in Garbage.. and he sold to waste management for 65 million.. so not a billionaire but well off .. he paid his tax's had zero debt and the rest was in double tax free munis.. and all of his real estate holdings in and around Napa were paid for as well as his home up at Tahoe and his place in Kona and his hunting ranchs and his duck hunting ranch's etc etc.with his help I made it through the great recession.. but I am the first to admit I got my butt handed to me.. debt was not my friend and now I am pretty debt adverse other than construction loans that are all 15 months or less..

If not... these can be significant issues that can't be overcome (being historical).

If you don't panic but work through difficulties and overcome obstacles, you reduce your risk.I don't know how to quantify it on a scale because every deal and every investor is unique.

@Juan David Maldonado, Sentimental value is going to be a tough one to over come, however I would run the numbers and show her the possibilities.

You can overcome your weak areas by partnering with someone who is strong in them or going to work for someone and gain knowledge from them in those areas.

However, one of my concerns with this strategy is the possibility of an adverse relationship between partners.

Thank you for sharing your success story and mentioning that you have had challenges on the way that you ere able to overcome.

@David Finley,Check out your state laws on adverse possession.  

Additionally, I feel calling my contacts up on the weekly to discuss listings without being able to physically see the properties may exhaust the relationship.Have any of you faced this challenge, and if so, what techniques did you use to help overcome this?

By work out costs, do you mean fees paid to the servicer to negotiate modifications or other terms in the scenario of non-payment, default, or other adverse situation?