For Investors with several properties, that requirement can be difficult.     I

It will be miniscule compared to the neighborhood price comps, versus the skin of your house.As to appraisal or resale value, maybe a bit more just for the fact of having some fresh updates. 

You may also want to consider bringing 10% of purchase as well to give them a comfort level with your skin in the game But find an attorney, make sure they have drafted these docs before and pay for them. 

I looked and under that section this was the comment:"Due to the difficulty is accurately determining accrued depreciation of a complex of the subject's age and due to the limited availability of recent vacant land sales in the immediate submarket, the Cost Approach was deemed to be a very weak indicator for value for the subject, thus is was excluded from this analysis.

Any creative ideas on how to make this work where he would have some skin in the game and I could ensure he is diligently trying to purchase a home?

The difficulty in dealing with the local agencies is one reason Tahoe home prices tend to stay stronger than the overall market.

But if the nightly news covered every bad renter, I bet it would be a 100:1 ratio and people would be amazed by what Landlords put up with.Again, it's no skin off my nose.

Generally replace however there is an appliance shortage going on currently so getting a new one that fits could be difficult. I

Overall I see some general difficulty with vacancies.

You want a "friend" discount early which is not in the seller's best interests unless there are difficulties with the sale or other anomalies that you are willing to take on, and even in that case, they could probably still do better on the market unless you are willing to pay up early so it doesn't hit the market.Too many people try to push the blame onto agents.