@Jamie Dupont From a tax perspective, you can deduct repair expenses related to the damages caused by the tenant as long as they’re for restoring the property (e.g., fixing holes, broken fixtures).

The digital world is full of different perspectives and this is already more time than I care to share on this topic any more.

I expect that I'll be reserving time in various resorts and farming those weeks out to perspective vacationers, does anyone know if VRBO, or AirBnB, or some other site would be most appropriate for this approach?

However, my perspective is more cautious, driven not just by statistical analysis but by firsthand observations in the field and insights from investors and developers across the country.

My background as a prior military member has instilled in me a sense of discipline, strategic planning, and a keen understanding of risk management.While I’m aware that financial contributions are often key in partnerships, I’m curious about what other skills and perspectives I can bring.

Sounds like you have a great perspective! 

The best answer I found was looking at it from a tax and legal perspective.

They are subject to a credit, criminal, and eviction check just like other perspective tenant candidates.One thing I would suggest is asking them how much their subsidy is for.  

Does anyone have any updated perspectives on this area now? 

It's helpful to hear the perspective outside the broker.