Like others have mentioned, you will pay structurally more for a home warranty than self-insuring for the cost of repairs.This may be worth it if the value proposition was that you could be hands-off whenever a covered item breaks.In reality, it adds significant overhead because there is the claims process and you give up control of the repair timeline and quality as you have discovered.

Own (or Control) more stuff that puts money in your pocket today or in the future.

Can you manage the effort and keep costs under control?  

I've never stayed in a hotel or short term rental where I couldn't control the temperature.

Assignment is the legal term and is not limited to the length of time the property is owned or controlled by the assignee.

Since my grandpa's wife is passed already, he has full control of the property, but if he were to sell the house, he would have to pay his wife's family a percentage of the sale, but he doesn't want to do, he would rather take out some type of loan (what loan is best in this situation?)

This is a really significant strategy, because getting control of even two or three buildings can change the course of your financial future.

Thanks for the reply.I live in the Los Angeles area (Orange County to be precise).

This situation was beyond my control and I took quick, aggressive action. 

You talked about location and size, but how are the things you can control?