If I know the roof is half way in it's life-cycle, I will probably save up a lot more than 5% for cap ex. 

What's important to notice is how short the adoption lifecycle is for nascent tech.

They do their own due diligence, have their own analysts, do their own modeling, create their own PPM, marketing materials, tour the property w/the operator to understand clearly the business plan, making suggestions on strategy, maintain the relationship with the investor base over the entire life cycle of the deal, creating reports, answering questions, managing distributions, K1s, etc. 

The tear off and replacement is the last step in the life cycle of a roof. 

A typical life cycle might be 5- 7 years from start to finish. 

I also believe in having the rainy day fund accumulate for the eventual repairs and larger lifecycle replacements. 

The idea there would be, is it fair to the sons to burden them with a almost a full life cycle of the loan for a debt that grandpa as PR and Mortgagee had material knowledge of, failed to deal with but still may be entitled to some form of recovery?  

Increasing your touches with every person in your business life cycle is never a bad idea.

If you are looking to invest in tax lien certificates, at any point in their lifecycle, let me know.

If you have one section that is asphalt shingle and another that is copper, you won't be taking advantage of the long lifecycle because you'll still have to replace the shingles more often.