A survey of housing charities shows that Door County isn't alone in its troubles
The Door County Housing Partnership participated in a survey which included a lot of similar organizations over most of the 50 states.
The survey indicates that the situation with short term rentals and with gentrification is worse in some other communities than in Door County. The pie charts for question nine on the bottom of https://udspace.udel.edu/server/api/core/bitstreams/b3cab232-e20b-42e3-a370-2fb52c50043e/content#page=65 shows that the percentage of short term rentals are even higher in some places than they currently are in Door County. Some communities have been able to oppose short-term rentals with laws:
Some localities have quantitative or locational restrictions against [short-term rentals] to ensure housing for permanent residents and low-to-moderate workers. The need for these types of restrictions may be present in coastal communities with high rates of short-term rentals. For example, 45% of Lewes, Delaware’s housing stock is not occupied full-time, indicating a strong presence of housing like short-term rentals.
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Except for the bar graph with the figures for city of Sturgeon Bay, https://www.co.door.wi.gov/DocumentCenter/View/1679/Chapter-4-Housing#page=6 shows that Door County’s housing vacancy rate is considerably higher, using 2010 census results.
Looking at the survey results from https://udspace.udel.edu/server/api/core/bitstreams/b3cab232-e20b-42e3-a370-2fb52c50043e/content#page=78, it seems that many similar organizations similar to the Door County Housing Partnership report a low level of financial support. This raises the question whether it will ever be financially supported enough.
https://udspace.udel.edu/server/api/core/bitstreams/b3cab232-e20b-42e3-a370-2fb52c50043e/content#page=92 discusses how gentrification can impact the efforts of charitable organizations. It explains that the motivation of the donations is because wealthy customers want those who serve them to have good housing.
Reflecting on this in the long run, I wonder about how giving would interact with the automation of service jobs. If it is the only motivation, charitable efforts will stagnate, because not interacting with humans holding service jobs as much will undermine motivation.
The discussion on the page 92 link implies that if it wasn’t for gentrification, the charities would have an easier time helping out. It follows that if charity is combined with government reforms, the outcome will be even better than with charity alone. What is really needed is to change the tax system and adjust economic policy to solve the gentrification problem.