While I do maintain a relatively modest percentage of my assets in money market instruments, corporate debt funds, and high dividend stocks, I remain most comfortable with the investments I specialize in and know best.  

Small is easy to maintain as long as renovations were done correctly.

If an LLC is the best way to go, should I create the LLC in Idaho using an address I plan to maintain in Idaho?

Then rent the bigger home out using a property manager, allowing her to possibly cash flow and maintain that asset and let it continue to grow in value.Encourage her to consult with a CPA or tax attorney to explore the best strategy tailored to her situation.

If maintaining cash flow is your primary objective, you might want to explore other options.

Lots of people who have trailers don't own the property they are on and sell them.As for the owner of the land expecting tenants to do repairs-there shouldn't be many repairs required to the land, just the trailer that is on it (which your grandmother owns and should be responsible for maintaining). 

It would for sure have to be a higher hourly rate than a typical W2 job however as agents are 1099 contractors and there are expenses associated with maintaining our licenses and operating our businesses that usually come out of our commissions.

You can purchase them yourself and just hire an HVAC tech to install to save money, but it's going to cost more plus you'll have to maintain them. 

Unless your deals are particularly complex or unique, why would anyone pay to maintain their loan documents anymore?

From my experience, section 8 tenants will go above and beyond to maintain their section 8 support if it becomes at risk.