When I have a situation like this, I give them a written notice to accept the property in its current condition or get out.

Assumptions: specifically allowed in city ordinances, mobile home manufacturing in the area, or that someone heavily marketed that area as a retirement location in the past. 

Stats can be foundhttps://www.ramaui.com/housing-statisticsOr for all islands herehttps://www.hawaiirealtors.com/resources/housing-trends-2/Your realtor can produce more specific stats on your area of interest.

- Are there specific tools, resources, or methods you use to simplify the regulation process?

Unfortunately many landlords take the first group they find in these situations and come from the ideology that all college students are slobs so no sense offering anything nice. 

Building department can advise on specific next steps - municpal hearing and presentation of plans will be required in most cases. 

I think it's going to be location specific for sure; where I am very few people hang out in the house all day long as they are usually busy hitting the parks and attractions. 

Home warranties can sometimes cover rental properties, but it really depends on the specific terms of the warranty and the provider.

@Mindy Jensen - I’m a GC from California, specifically the SF Bay Area.

That said, there are specific contractors who like working with investors since they can avoid the hassle of working on occupied homes.