My thinking is if a house that I buy today for $260k will be worth $500k in 20 years and I only have ~ $108k left on the original $190k mortgage, it will be a fairly easy payoff in those future dollars.

Pros:Stable Income: These facilities often sign longer leases, providing landlords with a more stable and predictable income compared to traditional residential rentals.Higher Rent Potential: Because these facilities generate income through the services they provide, landlords might negotiate higher rent than standard residential properties, reflecting the commercial nature of the tenant's business.Lower Tenant Turnover: Residential assisted living facilities tend to have lower turnover rates, reducing the frequency of vacancies and the costs associated with finding new tenants.Social Contribution: By renting to such facilities, landlords contribute to addressing the growing demand for assisted living and support services, positively impacting their community.Property Maintenance: Tenants in this sector often maintain the property well to comply with regulations and ensure a comfortable living environment for their clients, potentially reducing wear and tear.Cons:Regulatory and Compliance Issues: Facilities must adhere to strict regulatory and compliance standards, which can involve the landlord in complex legal and zoning issues.Higher Insurance Costs: The nature of the business might require additional insurance coverage, potentially increasing costs for landlords if they are responsible for carrying this insurance.Modifications and Upgrades: Meeting the specific needs of an assisted living facility may require significant property modifications and upgrades, which can be costly.Market Limitations: Should the lease end or the facility close, the specialized modifications made to the property might limit the market for future tenants, potentially requiring substantial investment to revert the property to standard residential use.Operational Oversight: Landlords might need to monitor the facility's operations more closely to ensure compliance with lease terms and local regulations, requiring more hands-on involvement than traditional rentals.I know tons of investors who are renting out their properties using this strategy here in Fort Worth. 

Also, consider the location within the resort -is the home strategically near the clubhouse, or does it have a great forest or lakefront view?

It may not be worth the trouble and cost of selling!

Okay thanks it was worth a shoot.

We used to offer this service to investors but it created more problems than it was worth. 

Definitely worth a call. www.Excel1031.com

If it’s a hotel, it prob won’t compete with homes w multiple bedrooms .. worth digging into

Definitely consult with your accountant before you sell as there are situations where a 1031 isn't worth it. 

We've done this so many times now, it's just part of the process and worth it in most cases.