The answer is relatively simple, it's landlord fatigue.  

His reason was the only thing he knew to do with the proceeds was to loan it back out at 12%, and he would be "behind" where he is now in cashflow.His proceeds would have given him options up to and including PE, but he is a simple man and in his case holding was the option for now. 

It's not as simple as homes that were burned being rebuilt and original owners returning to them.

I also agree that RE appreciation is unlikely to match the last dozen years, but you never know.Where I am unsure we agree is that paying $450k to improve the cash flow ~$3k (your numbers but I expect my delta wold be similar meaning both my cash flow estimates would be worse than yours but both would be worse by the same amount not affecting the difference) makes sense especially if the cost of having the extra $450k is only 6% rate which is historically simple to beat via numerous investment options and hopefully no one is investing in RE for an expected of 6%.  

But they are simple, respond quickly to questions, Lloyds is their underwriter, etc. 

Keep it simple - sell the property and let each sibling do what it is that they want.If you keep it and do a refinance(to pay for the bills)Who will be on the loan, will it impact everyoen's DTI?

Simple, reasonable action and patience. 

They used to be good and simple. 

Do you still recommend using a real estate CPA or is their tax professionals that specialize in the more simple investor situations like mine?

Simple and powerful.