This included paying for storage pods, hiring movers to help pack and load her belongings, and purchasing flights for Anna and her adult son, who has special needs.

I also require my tenants of any length (I only rent for 30+ days) to have their own renters insurance for their own belongings so I don't see any big issue with having your part-time tenants get renters insurance and then making sure that your own homeowners policy is aware that there are others living in your home but that they have separate renters insurance.

I should mention I already plan on finding out their expertise in real estate investing and local law, but my concern is how to decide which questions/topic belong in an initial consultation.

If there is no listing agent (at least) or selling agent, then the next deepest pockets belong to the bank and as a professional real estate associated organization they can not blame you for queering the deal as a civilian (for lack of a better term).

I need some advice on the materials to use in these updates because I know they need to be long lasting and durable but I can't help wanting to put some nicer elements that may not be as renter friendly.

It belongs to the tenants.

Damage to furnishings and other belongings is always a possibility in an MTR, just as it is in an STR.

Rows of debris and personal belongings line the streets, and upon closer inspection, some of it resembles a yard sale.It’s heartbreaking to see people throwing away brand-new TVs, washers, dryers, paintings, family photos, and boxes of clothes.

Simplest explanation is if something happens (eg a fire), your insurance isn't going to cover any of their belongings or temporary accommodation. 

I often wonder if the remote location (20 minutes up the mountain) is a turnoff and travelers are starting to prefer motel-like accommodations that are close to the main highways.Houses in the middle of the woods with no view, houses that are non-cabin style like they belong in a normal major city suburb, no game room, no deck to take in the view, no hot tub, no area for a fire pit, no room for extra activities like corn hole or throwing the football, poor driveway, steep entrance, tons of stairs etc.