Luckily they have been accommodating and wanting the updates and willing to pay more for those... so far.

Permits required unless zoned for accommodations.  

I have quite a few clients who self manage their vacation rentals from the mainland.Here is info directly off state of Hawaii website pertaining to vacation rentals (bold in mine):  If you’re off-island, you’ll need to designate a local contact who resides on the same island as the transient accommodation.

Let them know your trying to accommodate them and get everything fixed asap.

Sure, it may be zoned for an ADU, but does it have the lot size to accommodate an ADU to meet the setback requirements?

If it is still 30 days or same time period just a week late I would probably do nothing and be accommodating.

I am thinking about turning the house into place that can accommodate home health care.

Being flexible and accommodating is the way to go if you can.

Prior to this new surcharge by the HOA, we currently pay CO General Sales & Use Tax of 2.9%, Grand County General Sales & Use Tax of 1.3%, Grand County Accommodations Tax of 1.8%, and Granby City General Sales & Use Tax of 4%.

I know it will be hard to accommodate everyone's schedule with a group like this.