I consider the age of the product, the cause of the damage (gross negligence, abuse, or accident), the length of tenancy, and how the Tenant behaved in other aspects (timely rent, communicative, no lease violations, etc.). 

Estimated length of stay?

I suppose its not fully arms-length since there is one investor, but that's an IRS / taxation issue. 

I feel like due to the length of ownership and that amount still owed on the mortgage (to be paid back at time of sale) they'll be most likely looking at little to no capital gains.

Small (1cm in length about) with a yellow ish stripe in the center of the back is a German roach.

But “back in the day” the bank’s contract would say that it had to be an arm’s length transaction, AND the short seller could not receive any benefits/money. 

If the goal is to use real estate and/or notes to better secure and grow a portion of your father's IRA, there are probably ways you can tap into your expertise and network to find him places he can make investments that fit the IRS definition of "arm's length".

Prepayment penalties range from 1-5 years and you get to decide the length of the term.

Length of Listing.Get at least a 6 month listing and be sure that there is no charge for cancellation.

Length of prepayment penalty- Generally prepayment penalties run from 1-5 years.